Methyl 3-aminocrotonate → HCID 13752662, compound

HRID 845273Notes

Reaction equation

HRID 845273 reaction equation
[C:1]1(=[O:36])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15](=[O:30])[C:16](=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:17]([CH3:19])=O)[C:4](=[O:31])[C:3]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:2]12.[CH3:37][O:38][C:39](=[O:44])/[CH:40]=[C:41](\[NH2:43])/[CH3:42]>C(O)(C)C>[CH3:42][C:41]1[NH:43][C:17]([CH3:19])=[C:16]([C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:5]2[C:1](=[O:36])[C:2]3=[CH:35][CH:34]=[CH:33][CH:32]=[C:3]3[C:4]2=[O:31])=[O:30])[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:40]=1[C:39]([O:38][CH3:37])=[O:44]

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 53663610HCID 53663610, compound

Product 1

HCID 13752662HCID 13752662, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6.68 g (13.6 mmol) of 2-(3-nitrobenzylidene)-acetoacetic acid-(8-phthalimidooctyl)ester and 1.57 g (13.6 mmol) of 3-amino-crotonic acid methyl ester are boiled under reflux in 70 ml of isopropanol for 5 hours. The oil obtained after removal of the solvent by evaporation under vacuum is chromatographed on silica gel with dichloromethane/methanol (97:3) as solvent. 6.75 g (85%) of a yellow oil are obtained.

Workup

  1. customThe oil obtained
  2. customafter removal of the solvent
  3. customby evaporation under vacuum
  4. customis chromatographed on silica gel with dichloromethane/methanol (97:3) as solvent

Sources & evidence

ORD record
ord-4a0e3df3f8924c209e7022b24d1f226c
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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