Acetone → 2-(N-isopropylamino)-4-methylbenzophenone
Reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:17][C:18]([CH3:20])=O.[BH4-].[Na+]>C(O)(=O)C>[CH:18]([NH:1][C:2]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])([CH3:20])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 21.1 gms. of 2-amino-4-methylbenzophenone in 100 mls. of acetone is added 100 mls. of glacial acetic acid. The solution is cooled to 20° C. With stirring, and by portionwise addition, 10 gms. of sodium borohydride is added to the solution over a period of 70 minutes. After the addition, the solution is stirred for an additional 20 minutes at 20° C., and extracted with 100 mls. of chloroform and 50 mls. of water. The aqueous phase is extracted twice using 50 mls. of chloroform each time. All the chloroform solutions are then combined and treated with 150 mls. of 20% ammonium hydroxide. The chloroform phase is dried over magnesium sulphate, filtered and concentrated by distillation to a constant weight of 25 gms or a crude 99% yield of 2-(N-isopropylamino)-4-methylbenzophenone, providing an actual yield of pure material of at least 90%.
Workup
- additionby portionwise addition, 10 gms
- additionAfter the addition
- stirringthe solution is stirred for an additional 20 minutes at 20° C.
- extractionextracted with 100 mls
- extractionThe aqueous phase is extracted twice
- additiontreated with 150 mls
- dry with materialThe chloroform phase is dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated by distillation to a constant weight of 25 gms
Sources & evidence
- ORD record
- ord-45a96ad3053e4fd6b66ca944444e9aab
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04083871
Reaction notes
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