HCID 20371721, compound → HCID 20371608, compound

HRID 616213Notes

Reaction equation

HRID 616213 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:28]=[CH:27][C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=2[OH:26])[CH:15]([OH:22])[CH2:16][NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:10])=[CH:7][CH:6]=1)([O-])=O.[H][H]>O=[Pt]=O.CO>[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=2[OH:26])[CH:15]([OH:22])[CH2:16][NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:10])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 20371721HCID 20371721, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20371608HCID 20371608, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(4-nitrobenzamido)-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride (7.37 g, 0.018 mole), PtO2 (250 mg), and methanol (225 ml) was placed in a pressure hydrogenation apparatus at a starting pressure of 2 atm. The hydrogenation was started, and the calculated amount of hydrogen was taken up within 17 minutes. The hydrogenation was interrupted and the platinum catalyst was filtered off. The clear colorless filtrate was evaporated on a rotary evaporator at 40° - 50° C. The residue, a cream-colored foam (7.3 g), was recrystallized three times from methanol/ether, and 3.50 g (50%), m.p. 228.8° - 230° C, of analytically pure 3-(4-aminobenzamido)-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride, was obtained.

Workup

  1. filtrationthe platinum catalyst was filtered off
  2. customThe clear colorless filtrate was evaporated on a rotary evaporator at 40° - 50° C
  3. customThe residue, a cream-colored foam (7.3 g), was recrystallized three times from methanol/ether, and 3.50 g (50%), m.p. 228.8° - 230° C

Sources & evidence

ORD record
ord-56b7f56aae0d4cc6afcd2e75011e23e2
Source dataset
uspto-grants-1978_02
Patent number
US04072760

Reaction notes

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