Acetic Acid → 5-Methyl-7-(3-nitrophenyl)-1,2,3,7-tetrahydroindolizine-6,8-dicarboxylic acid 6-methyl ester 8-ethyl ester

HRID 972880Notes

Reaction equation

HRID 972880 reaction equation
CO[C:3](=O)[CH2:4][C:5]([CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=O.[C:19]([CH:24]=[C:25]1[CH2:29]C[CH2:27][NH:26]1)([O:21][CH2:22]C)=[O:20].[CH2:30]([OH:32])[CH3:31].[C:33](O)(=[O:35])C>>[CH2:30]([O:32][C:33]([C:7]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:24]([C:19]([O:21][CH3:22])=[O:20])=[C:25]([CH3:29])[N:26]2[C:5]=1[CH2:4][CH2:3][CH2:27]2)=[O:35])[CH3:31]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 534430103-Nitrobenzylideneacetoacetic acid methyl esterHCID 68118984Ethyl (pyrrolidin-2-ylidene)acetate

Product 1

HCID 544330685-Methyl-7-(3-nitrophenyl)-1,2,3,7-tetrahydroindolizine-6,8-dicarboxylic acid 6-methyl ester 8-ethyl esterYield 73%

Procedure

Upon boiling a solution of 8.3 g of 3-nitrobenzylideneacetoacetic acid methyl ester and 5.6 g of 2-carbethoxymethylidenepyrrolidine in 50 ml of glacial acetic acid for 8 hours, 5-methyl-7-(3-nitrophenyl)-1,2,3,7-tetrahydroindolizine-6,8-dicarboxylic acid 6-methyl ester 8-ethyl ester of melting point 120° (ethanol) is obtained.

Workup

  1. customfor 8 hours

Sources & evidence

ORD record
ord-397e99adca814d3a91419312a8381683
Source dataset
uspto-grants-1977_10
Patent number
US04053614

Reaction notes

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