Methyl 3-aminocrotonate → HCID 10669204, compound

HRID 1073359Notes

Reaction equation

HRID 1073359 reaction equation
[C:1]([C:4](=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[C:5]([O:7][CH:8]([CH3:11])[CH2:9][Cl:10])=[O:6])(=O)[CH3:2].[NH2:22]/[C:23](/[CH3:29])=[CH:24]\[C:25]([O:27][CH3:28])=[O:26]>C(O)(C)C.C(OCC)C>[CH3:29][C:23]1[NH:22][C:1]([CH3:2])=[C:4]([C:5]([O:7][CH:8]([CH3:11])[CH2:9][Cl:10])=[O:6])[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 53673654HCID 53673654, compound

Product 1

HCID 10669204HCID 10669204, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A solution comprising 18.72 g of 1-methyl-2-chloroethyl α-acetyl-3-nitrocinnamate, prepared as described in Example 1, and 7.12 g of methyl 3-aminocrotonate in 48 ml of isopropanol was refluxed under stirring for 210 minutes. After cooling, the reaction mixture was evaporated to dryness under vacuum and the oil thus obtained was chromatographed on silica gel (200 g) using chloroform as eluent. Evaporating the fractions containing a sole product (TLC, chloroform: ethylacetate 95:5) gave a thick oil, which was dissolved in diethyl ether. The solvent was then evaporated off at 20°-25° C. to give 15.75 g of the title compound, m.p. 95°-102° C., which could be employed without further purification.

Workup

  1. customprepared
  2. temperaturewas refluxed
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated to dryness under vacuum
  5. customthe oil thus obtained
  6. customwas chromatographed on silica gel (200 g)
  7. customEvaporating the fractions
  8. additioncontaining a sole product (TLC, chloroform: ethylacetate 95:5)
  9. customgave a thick oil, which
  10. customThe solvent was then evaporated off at 20°-25° C.

Sources & evidence

ORD record
ord-9a9d5351d54b4735a6994d21368b0a44
Source dataset
uspto-grants-1990_11
Patent number
US04968832

Reaction notes

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