3-Bromoaniline → N-(3-Bromophenyl)-3-oxobutanimidic acid

HRID 279998Notes

Reaction equation

HRID 279998 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH2:9]=[C:10]1[O:14][C:12](=[O:13])[CH2:11]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:13])[CH2:11][C:10](=[O:14])[CH3:9])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 12661Diketene

Product 1

HCID 285615N-(3-Bromophenyl)-3-oxobutanimidic acidYield 49.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a heated (80° C., oil bath temperature) solution of 20.00 g (0.12M) of m-bromoaniline in 200 mL of dry toluene was added dropwise over a period of 30 min. 12 g (0.14M) of diketene in 100 mL of dry toluene. When the addition was completed, the reaction mixture was brought to reflux for 5 h. The toluene was then removed in vacuo, resulting in a yellow solid. Recrystallisation from toluene afforded 14.70 g (48%) of product as light pink crystals: mp 94°-95° C.

Workup

  1. additionwas added dropwise over a period of 30 min
  2. additionWhen the addition
  3. temperatureto reflux for 5 h
  4. customThe toluene was then removed in vacuo
  5. customresulting in a yellow solid
  6. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-2dff6fe20a1e491d9bf32bb7580f4301
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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