Methyl 3-aminocrotonate → HCID 10347672, compound

HRID 483201Notes

Reaction equation

HRID 483201 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[C:21]([O:27][CH2:28][C:29]([CH3:41])([CH3:40])[CH2:30][N:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32])(=[O:26])[CH2:22][C:23]([CH3:25])=O>CC(O)C>[CH3:25][C:23]1[NH:13][C:14]([CH3:20])=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[Cl:1])[C:22]=1[C:21]([O:27][CH2:28][C:29]([CH3:41])([CH3:40])[CH2:30][N:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32])=[O:26]

Participants

5

Reactant 3

HCID 643918Methyl 3-aminocrotonateHCID 10108340HCID 10108340, compoundHCID 126677132-Chloro-3-nitrobenzaldehyde

Product 1

HCID 10347672HCID 10347672, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 128.7 mg of 2-chloro-3-nitrobenzaldehyde, 88 mg of methyl 3-aminocrotonate and 220 mg of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl acetoacetate in 1 ml of 2-propanol was refluxed for 8 hours, and then the solvent was distilled off under reduced pressure. The residue was purified by a column chromatography on silica gel to yield 200 mg of desired compound (136).

Workup

  1. temperaturewas refluxed for 8 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-5085f0ec63264fc68ea07d1696a645f9
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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