Sodium Hydroxide → HCID 68145152, compound

HRID 1730387Notes

Reaction equation

HRID 1730387 reaction equation
[CH:1]([NH:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)=O.[H-].[Al+3].[H-].[H-].[H-].[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>C(O)(C)C.O.C(OCC)(=O)C.CCOCC>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[CH3:1][NH:3][CH2:4][CH:5]1[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 202619Formamide, N-((5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-HCID 444266Maleic AcidHCID 21584524Aluminiumhydride

Product 1

HCID 68145152HCID 68145152, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Formamidomethyl-5H-dibenzo[a,d]cycloheptene (3.80 g., 0.015 mole), dissolved in 400 ml. of absolute ether is added gradually to a solution oflithium aluminum hydride (0.87 g., 0.023 mole) in 45 ml. of absolute ether at a rate such that gentle refluxing is maintained. The reaction mixture, containing a precipitate, is heated to refluxing with stirring for 26 hours. After cooling to room temperature, 10 ml. of ethyl acetate is addedto decompose the excess hydride. Water, 1 ml., 15% sodium hydroxide, 1 ml. and water, 3 ml. then are added to the vigorously stirred reaction mixture. After standing several days, the reaction mixture is filtered andthe solid washed several times by suspension in ether. The combined filtrates and ether washings are evaporated on a film evaporator under reduced pressure, the pale yellow oily residue is dissolved in dilute hydrochloric acid, the solution extracted with ether to remove non-basic material, then rendered alkaline and the product extracted with ether. After washing with water and drying over anhydrous sodium sulfate, the ether is evaporated on a film evaporator under reduced pressure. The yellow oily residue weighs 3.05 g. A 2.95 g. portion is dissolved in isopropyl alcohol and a solution of 1.60 g. (0.0138 mole) of maleic acid in 5 ml. of isopropyl alcohol is added. The hydrogen maleate salt of the product separates out in white crystals. It melts at 163°-164° C. (clears, 165° C.) after further recrystallization from isopropyl alcohol and drying in vacuo over phosphorus pentoxide.

Workup

  1. temperatureis maintained
  2. additionThe reaction mixture, containing a precipitate
  3. temperatureis heated
  4. temperatureto refluxing
  5. additionthen are added to the vigorously stirred reaction mixture
  6. waitAfter standing several days
  7. filtrationthe reaction mixture is filtered andthe solid
  8. washwashed several times by suspension in ether
  9. customThe combined filtrates and ether washings are evaporated on a film evaporator under reduced pressure
  10. dissolutionthe pale yellow oily residue is dissolved in dilute hydrochloric acid
  11. extractionthe solution extracted with ether
  12. customto remove non-basic material
  13. extractionthe product extracted with ether
  14. washAfter washing with water
  15. dry with materialdrying over anhydrous sodium sulfate
  16. customthe ether is evaporated on a film evaporator under reduced pressure
  17. dissolutionportion is dissolved in isopropyl alcohol
  18. customIt melts at 163°-164° C. (clears, 165° C.) after further recrystallization from isopropyl alcohol
  19. dry with materialdrying in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-cc8ac0036ba54d9a95d434d4e415a853
Source dataset
uspto-grants-1976_11
Patent number
US03992445

Reaction notes

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