Ethanol → 1-Acetyl-4-(2-amino-4-chlorophenyl)-2,3-dihydro-1H-pyrrole-2,2-dicarboxylic acid diethylester

HRID 1390835Notes

Reaction equation

HRID 1390835 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[N+:18]([O-])=O)=[CH:8][N:7]1[C:21](=[O:23])[CH3:22])=[O:5])[CH3:2].C(O)C>O1CCCC1.CO.[Pt]>[CH2:1]([O:3][C:4]([C:6]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[NH2:18])=[CH:8][N:7]1[C:21](=[O:23])[CH3:22])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 702EthanolHCID 128784981-Acetyl-4-(4-chloro-2-nitrophenyl)-2,3-dihydro-1H-pyrrole-2,2-dicarboxylic acid diethyl ester

Product 1

HCID 128785021-Acetyl-4-(2-amino-4-chlorophenyl)-2,3-dihydro-1H-pyrrole-2,2-dicarboxylic acid diethylester

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 82.2 g (0.20 mol) of the compound of Example 10 in 300 ml of tetrahydrofuran and 700 ml of methanol was hydrogenated in the presence of 4 g of 5% sulfided platinum on carbon at room temperature and 1500 psi for 22 hours. The reaction mixture was concentrated and the solid residue (76 g) was recrystallized from ethanol (320 ml) to afford 61.4 g (81%) of light orange crystals, m.p. 151.5-153°. The analytical sample was prepared by a second recrystallization from ethanol: white crystals, m.p, 152-153.5°.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe solid residue (76 g) was recrystallized from ethanol (320 ml)
  3. customto afford 61.4 g (81%) of light orange crystals, m.p. 151.5-153°
  4. customcrystals, m.p, 152-153.5°

Sources & evidence

ORD record
ord-f90499345ffe482885377595ef40879b
Source dataset
uspto-grants-1979_02
Patent number
US04140697

Reaction notes

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