Ethyl Acetate → HCID 12690621, compound

HRID 1730972Notes

Reaction equation

HRID 1730972 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[CH2:8][CH2:7][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[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 12690616HCID 12690616, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12690621HCID 12690621, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8 g. of freshly prepared 5-hydrazinomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol, 40 mg. of platinum dioxide, 120 ml. of ethyl acetate and 40 ml. glacial acetic acid is hydrogenated at room temperature and about atmospheric pressure until the uptake of hydrogen is about stoichiometric. The resulting mixture is filtered, evaporated in vacuo and the residue taken up in 400 ml. of chloroform, made neutral by shaking with 10% sodium bicarbonate solution, and the aqueous phase discarded. The organic phase is extracted twice with water and then with saturated sodium chloride solution, followed by drying and evaporation in vacuo to about 50 ml. to effect crystallization which is completed by adding 50 ml. of diethyl ether to obtain 5-aminomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol, m.p. 147°-149° C.

Workup

  1. additionA mixture of 8 g
  2. customis hydrogenated at room temperature
  3. filtrationThe resulting mixture is filtered
  4. customevaporated in vacuo
  5. extractionThe organic phase is extracted twice with water
  6. customby drying
  7. customevaporation in vacuo to about 50 ml
  8. customto effect crystallization which
  9. additionby adding 50 ml

Sources & evidence

ORD record
ord-3ae86688484f498faf9ce4ee812e91c1
Source dataset
uspto-grants-1976_11
Patent number
US03994918

Reaction notes

Loading…