Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoate → HCID 20132493, compound

HRID 845277Notes

Reaction equation

HRID 845277 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:5]([CH3:7])=O.[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:34])/[CH:30]=[C:31](\[NH2:33])/[CH3:32])#[N:20]>C(O)(C)C>[CH3:7][C:5]1[NH:33][C:31]([CH3:32])=[C:30]([C:29]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:19]#[N:20])=[O:34])[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:4]=1[C:3]([O:2][CH3:1])=[O:18]

Participants

4

Reactant 2

HCID 1536427Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoateHCID 20132525HCID 20132525, compound

Product 1

HCID 20132493HCID 20132493, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6.7 g (26.8 mmol) of 2-(3-nitrobenzylidene)-acetoacetic acid methyl ester and 6.0 g (26.8 mmol) of 3-amino-crotonic acid-(7-cyanoheptyl)ester are boiled in 50 ml of isopropanol for 12 hours. The precipitate which separates is suction filtered and chromatographed on silica gel with dichloromethane/methanol (98:2). The main fraction yields 7.9 g (65%) of yellow crystals melting at 151°-152° C. after concentration of the fraction by evaporation under vacuum and recrystallisation of the residue from tert.-butyl-methyl ether.

Workup

  1. filtrationfiltered
  2. customchromatographed on silica gel with dichloromethane/methanol (98:2)

Sources & evidence

ORD record
ord-9a0c8e2668d743789735cefc305d03fa
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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