HCID 21437965, compound → HCID 21437925, compound

HRID 2397411Notes

Reaction equation

HRID 2397411 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 21437965HCID 21437965, compound

Product 1

HCID 21437925HCID 21437925, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6 gm (0.02 mol) of 4-(4'-nitro-4-biphenylyl)-4-hydroxy-butyric acid in 200 ml of methanol were hydrogenated in the presence of 3 gm of Raney nickel as a catalyst, at room temperature and at a pressure of 5 atmospheres. After absorption of the calculated quantity of hydrogen, the catalyst was vacuum-filtered off and the solvent was distilled off. The residual 4-(4'-amino-4-biphenylyl)-4-hydroxy-butyric acid, after recrystallization from methanol, had a m.p. of 145° C. (decomp.). Melting point of the cyclohexylamine salt: 178° C. (decomp.; precipitated from ethyl acetate/absolute ethanol). Yield: 5.5 gm.

Workup

  1. customAfter absorption of the calculated quantity of hydrogen
  2. filtrationthe catalyst was vacuum-filtered off
  3. distillationthe solvent was distilled off
  4. customThe residual 4-(4'-amino-4-biphenylyl)-4-hydroxy-butyric acid, after recrystallization from methanol
  5. customMelting point of the cyclohexylamine salt: 178° C. (decomp.; precipitated from ethyl acetate/absolute ethanol)

Sources & evidence

ORD record
ord-59c3e3647eff4860b993827f296ce116
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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