Hydrochloric Acid → HCID 15240193, compound

HRID 1493839Notes

Reaction equation

HRID 1493839 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH:8]=[C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH:13]=[CH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-])=O.Cl.[OH-].[Na+]>[Fe].CN(C)C=O>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([CH:8]=[C:9]2[C:10]3[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=3[CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22617097HCID 22617097, compound

Product 1

HCID 15240193HCID 15240193, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

10.0 g (30.7 m moles) of 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene, 8.0 g (143 m moles) of reductive iron powder, and 2.70 ml (30.6 m moles) of concentrated hydrochloric acid (d: 1.18, 35%) were added to 150 ml of N,N-dimethyl formamide, and the mixture was heated at an inside temperature of about 70° C., and stirred at that temperature with heating for 3 hours. After the end of reaction, the mixture was cooled over an ice-water bath, admixed with about 12.4 ml of an aqueous 10% NaOH solution, stirred and subjected to filtration by suction. The filtrate was poured into about 1l of an aqueous saturated NaCl solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was removed therefrom under reduced pressure. The residue was admixed with methanol, and the precipitated crystal was recovered therefrom by filtration. The thus obtained crystal was recrystallized from methanol, whereby 8.41 g of 5-(4-aminobenzylidene)-5H-dibenzo[ a,d]cycloheptene was obtained (yield: 92.7%). The melting point was 119°-120.0° C. Elemental analysis as C22H17N was as follows:

Workup

  1. temperaturewith heating for 3 hours
  2. customAfter the end of reaction
  3. temperaturethe mixture was cooled over an ice-water bath
  4. stirringstirred
  5. filtrationsubjected to filtration by suction
  6. additionThe filtrate was poured into about 1l of an aqueous saturated NaCl solution
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was removed
  10. customthe precipitated crystal was recovered
  11. filtrationby filtration
  12. customThe thus obtained crystal was recrystallized from methanol

Sources & evidence

ORD record
ord-cd384bef78044a39af7aa84c42ac71e1
Source dataset
uspto-grants-1991_06
Patent number
US05024912

Reaction notes

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