2,3-Dichlorobenzaldehyde → HCID 10325127, compound

HRID 483200Notes

Reaction equation

HRID 483200 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:11]/[C:12](/[CH3:18])=[CH:13]\[C:14]([O:16][CH3:17])=[O:15].[C:19]([O:25][CH2:26][C:27]([CH3:39])([CH3:38])[CH2:28][N:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:30])(=[O:24])[CH2:20][C:21]([CH3:23])=O>CC(O)C>[CH3:23][C:21]1[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=2[Cl:1])[C:20]=1[C:19]([O:25][CH2:26][C:27]([CH3:39])([CH3:38])[CH2:28][N:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:30])=[O:24]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 10108340HCID 10108340, compound

Product 1

HCID 10325127HCID 10325127, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 175 mg of 2,3-dichlorobenzaldehyde, 126 mg of methyl 3-aminocrotonate and 320 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 provide 260 mg of the desired compound (134).

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-8e8e9ef18bfc456ca47fff18a173e55a
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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