Citric Acid → Ethyl 3-amino-5-chloro-4-cyclohexylphenylglyoxylate

HRID 866837Notes

Reaction equation

HRID 866837 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[C:6]([N+:14]([O-])=O)[C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[H][H]>[Pd]>[NH2:14][C:6]1[CH:5]=[C:4]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 20515183Ethyl 3-chloro-5-nitro-4-cyclohexylphenylglyoxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20515138Ethyl 3-amino-5-chloro-4-cyclohexylphenylglyoxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 17.6 g. (0.05 moles) of ethyl 3-chloro-5-nitro-4-cyclohexylphenylglyoxylate in 100 ml. of methanol containing 0.05 moles of 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-5-chloro-4-cyclohexylphenylglyoxylate isolated as the citrate salt.

Workup

  1. additionA mixture of 17.6 g
  2. customare absorbed
  3. filtrationThe mixture is filtered
  4. washwashed with methanol
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-73eed884745348e4a3368066e07619cd
Source dataset
uspto-grants-1978_07
Patent number
US04101591

Reaction notes

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