Methanol → Ethyl 3-amino-4-cyclohexylphenylglyoxylate

HRID 444563

Reaction equation

HRID 444563 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([O-])=O.CO.[H][H]>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 20515200Ethyl 3-nitro-4-cyclohexylphenylglyoxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20515218Ethyl 3-amino-4-cyclohexylphenylglyoxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 15.3 g. (0.05 moles) of ethyl 3-nitro-4-cyclohexylphenylglyoxylate in 100 ml. methanol containing 0.05 mole citric acid and 1.5 g. of 5% palladium-on-carbon is shaken with hydrogen at 3 atm. pressure and 27° C. until 3 moles of hydrogen are absorbed. The mixture is filtered, washed with methanol and the filtrate concentrated in vacuo to obtain ethyl 3-amino-4-cyclohexylphenylglyoxylate, isolated as the citrate salt.

Workup

  1. additionA mixture of 15.3 g
  2. customare absorbed
  3. filtrationThe mixture is filtered
  4. washwashed with methanol
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f6a5e261b1bb49e8b2bba851a13e14ff
Source dataset
uspto-grants-1981_04
Patent number
US04264627

Linked notes

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