3-Chlorobenzaldehyde → HCID 69590140, compound

HRID 890157Notes

Reaction equation

HRID 890157 reaction equation
O=[C:2]([CH2:16][CH3:17])[CH2:3][C:4]([O:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5].[NH2:18]/[C:19](/[CH3:28])=[CH:20]\[C:21]([O:23][CH2:24][CH2:25][C:26]#[N:27])=[O:22].[Cl:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O>CC(O)C>[Cl:29][C:30]1[CH:31]=[C:32]([CH:33]2[C:20]([C:21]([O:23][CH2:24][CH2:25][C:26]#[N:27])=[O:22])=[C:19]([CH3:28])[NH:18][C:2]([CH2:16][CH3:17])=[C:3]2[C:4]([O:6][CH2:7][CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:5])[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 53744919HCID 53744919, compound

Product 1

HCID 69590140HCID 69590140, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

465 mg (2.0 mmol) of (3-phenyl-2-propene-1-yl) 3-oxovalerate, 309 mg (2.0 mmol) of (2-cyanoethyl) 3-aminocrotonate and 0.227 ml (2.0 mmol) of 3-chlorobenzaldehyde were heated at 70° C. under stirring in 10 ml of 2-propanol overnight. The reaction mixture was further heated at 120° C. under stirring under atmospheric pressure for 3 hours to evaporate 2-propanol. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

Workup

  1. customto evaporate 2-propanol
  2. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-5bc23c496da14600989a69d7d13f8bb8
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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