Nitroethane → HCID 22759464, compound
Reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:8]=1[CH:9]=O.[C:16]([O:23]C)(=O)[CH2:17][C:18]([O:20][CH3:21])=[O:19]>>[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:8]=1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH3:5].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:8]=1[CH:9]1[CH:4]([CH3:5])[NH:1][C:16](=[O:23])[CH:17]1[C:18]([O:20][CH3:21])=[O:19]Participants
Procedure
1-(2,6-Dichlorophenyl)-2-nitropropylene (m.p. 49°-50° C., b.p. 90°-102° C./0.33 mm. Hg.) is prepared from nitroethane and 2,6-dichlorobenzaldehyde by a similar process to that described in the second and third parts of Example 4. This compound is reacted with dimethyl malonate and the product hydrogenated by a similar process to that described in the fourth and fifth parts of Example 4, and the 4-(2,6-dichlorophenyl)-3-methoxycarbonyl-5-methylpyrrolidin-2-one thus obtained is separated into two geometrical isomers thereof by repeated chromatography on a silica gel column, using a 2:1 v/v mixture of toluene and ethyl acetate as eluant. The two isomers have m.p. 157°-158° C. (first isomer) and 143°-144° C. (second isomer). These two esters are separately hydrolysed and decarboxylated by a similar process to that described in the sixth part of Example 4, and there are thus obtained a first isomer, m.p. 182°-184° C., and a second isomer, m.p. 173.5°-175° C., of 4-(2,6-dichlorophenyl)-5-methylpyrrolidin-2-one, the isomers differing by cis- and trans- relationship of the 4-(2,6-dichlorophenyl)- and 5-methyl-subsitutents.
Sources & evidence
- ORD record
- ord-072983ebc72a4e64bea458025da5dd4c
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04126685
Reaction notes
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