Water → 3-(4-Amino-3-nitrophenyl)-1-phenyl-2-propen-1-one

HRID 2247863

Reaction equation

HRID 2247863 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].C([NH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[N+:24]([O-:26])=[O:25])(=O)C.O>C(O)C>[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:18][C:17]=1[N+:24]([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 291355N-(4-formyl-2-nitrophenyl)acetamide

Product 1

HCID 537490733-(4-Amino-3-nitrophenyl)-1-phenyl-2-propen-1-oneYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of acetophenone (7.2 g) and 4N-sodium hydroxide solution (14 ml) in ethanol (50 ml) was added 4-acetylamino-3-nitrobenzaldehyde (10.4 g) at ambient temperature under stirring and the resultant mixture was stirred at same condition for 2 hours. To the reaction mixture was added water and precipitate was collected by filtration. The precipitate was suspended in water (300 ml) and the resultant mixture was adjusted to pH 4.0 with 10% hydrochloric acid. The precipitate was collected by filtration and washed with brine and dried to give 3-(4-amino-3-nitrophenyl)-1-phenyl-2-propen-1-one (12.7 g).

Workup

  1. filtrationwas collected by filtration
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with brine
  4. customdried

Sources & evidence

ORD record
ord-02687328fc6f4df0b0f9d98ad9925211
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Linked notes

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