4-Butylaniline → Hexanamide, N-phenyl- (9CI)
Reaction equation
C([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)CCC.C(O[C:16](=[O:18])[CH3:17])(=O)C>O>[CH3:11][CH2:5][CH2:6][CH2:7][CH2:17][C:16]([NH:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:11][CH:10]=1)=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
One hundred grams of I, 4-n-butylaniline, were stirred with 500 grams H2O and 410 grams acetic anhydride added all at once. The temperature rose spontaneously to 45° C. and was raised briefly to 85° C, to bring all the solids into solution. Slow cooling, filtration, and overnight air drying gave 117.4 grams (92%) white plates of II, 4-butylacetanilide, mp 104°-105° C. (lit.1, mp 107° C). This 117.4 grams II were stirred with 486 grams acetic anhydride and 284 ml. 71% HNO3 added at such a rate that, after a brief induction period and with ice cooling, the temperature was kept at 30°-35° C. The reaction mixture was stirred 30 minutes at 5° C, then 300 grams ice, followed by 600 ml. H2O were added and the yellow solid filtered, washed copiously with H2O, and air dried to give 129.9 grams (90%) bright yellow III, 4-butyl-2-nitroacetanilide, mp 71°-73° C (lit.1, mp 76° C).
Workup
- additionadded all at once
- customrose spontaneously to 45° C.
- temperatureSlow cooling
- filtrationfiltration, and overnight air
- customdrying
Sources & evidence
- ORD record
- ord-8cbfbde81f104afda3f13b62fc800df7
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04060491
Reaction notes
Loading…