Hydrochloric Acid → HCID 23324916, compound

HRID 464731Notes

Reaction equation

HRID 464731 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][C:8](=[O:19])[NH:7]1.C[O:22][C:23](=[O:40])[CH2:24][CH:25]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[CH:26]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1.Cl>[OH-].[Na+]>[Cl:39][C:34]1[CH:33]=[C:32]([CH:25]([CH:26]2[CH2:30][CH2:29][C:28](=[O:31])[NH:27]2)[CH2:24][C:23]([OH:40])=[O:22])[CH:37]=[CH:36][C:35]=1[Cl:38].[Cl:18][C:13]1[CH:12]=[C:11]([CH:10]2[CH2:9][C:8](=[O:19])[NH:7][CH:6]2[CH2:5][CH2:4][C:3]([OH:20])=[O:2])[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 53908089HCID 53908089, compoundHCID 540793553-(3,4-Dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester

Product 2

HCID 23324916HCID 23324916, compoundHCID 23324918HCID 23324918, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 34.1 g of 3-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester and β-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester in 110 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (1 N, 120 ml) is added and the solution concentrated under reduced pressure to give β-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid, and 3-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid. The acids are dissolved in 100 ml of acetic anhydride, and the solution is heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to give cis- and transdihydro-1-(3,4-dichlorophenyl)-1H-pyrrolizine-3,5(2H, 6H)-diones as a white solid with mp 161°-167° C.

Workup

  1. concentrationthe solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e1d4df5245c450aacaa22c126010837
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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