Ethyl Acetate → HCID 12690623, compound

HRID 1730970Notes

Reaction equation

HRID 1730970 reaction equation
[NH:1]([CH2:3][C:4]1([OH:19])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)N.C(OCC)(=O)C.[H][H]>[Pt](=O)=O.C(O)(=O)C>[NH2:1][CH2:3][C:4]1([OH:19])[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 12690618HCID 12690618, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12690623HCID 12690623, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 6 g. of 5-hydrazinomethyl-5H-dibenzo[a,d] cyclohepten-5-ol, 160 mg. of platinum dioxide, 60 ml. of ethyl acetate and 60 ml. glacial acetic acid is hydrogenated at room temperature and about atmospheric pressure for 9 hours during which the uptake of hydrogen is about stoichimetric. The resulting mixture is filtered, evaporated in vacuo and the residue treated with 10% sodium bicarbonate solution and then with methylene chloride. The separated aqueous phase is extracted with methylene chloride and the combined organic phases extracted with water and then with saturated sodium chloride solution, followed by drying and evaporation in vacuo. The residue is crystallized from diethyl ether to obtain 5-aminomethyl-5H-dibenzo[a,d] cyclohepten-5-ol, m.p. 117°-120° C.

Workup

  1. additionA mixture of 6 g
  2. customis hydrogenated at room temperature
  3. filtrationThe resulting mixture is filtered
  4. customevaporated in vacuo
  5. additionthe residue treated with 10% sodium bicarbonate solution
  6. extractionThe separated aqueous phase is extracted with methylene chloride
  7. extractionthe combined organic phases extracted with water
  8. customby drying
  9. customevaporation in vacuo
  10. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-462809d4f73f458880f922adbc31f93f
Source dataset
uspto-grants-1976_11
Patent number
US03994918

Reaction notes

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