3-Bromoaniline → N-(3-Bromophenyl)-3-oxobutanimidic acid
Reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11]>C1C=CC=CC=1>[Br:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH:11][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
84 g of diketene were added over 20 minutes to a mixture of 172 g of m-bromo-aniline and 600 ml of benzene and the mixture was stirred for 5 hours at 20° C. The mixture was filtered and the precipitate was washed with benzene and isopropyl ether. The filtrate was vacuum filtered and evaporated to dryness to obtain 189 g of m-bromo-acetylacetanilide melting at 110° C.
Workup
- filtrationThe mixture was filtered
- washthe precipitate was washed with benzene and isopropyl ether
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-ea6e4e69366243ddac7c2fa6dbae45d2
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04014679
Reaction notes
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