Isatoic Anhydride → 2-Amino-N-(4-sec-butylphenyl)benzamide

HRID 1846275Notes

Reaction equation

[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[CH:13]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)([CH2:15][CH3:16])[CH3:14]>CN(C)C=O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:21][C:20]1[CH:22]=[CH:23][C:17]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:18][CH:19]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of isatoic anhydride (4.00 g, 24.0 mmol) in N,N-dimethyl formamide (80 mL) under nitrogen atmosphere was added 4-sec-butylaniline (3.66 g, 24.0 mmol). The reaction mixture was heated at 80° C. for 24 hours, then the solvent was removed under reduced pressure and the residue was diluted with ethyl acetate, washed with 1 N aqueous solution of sodium hydroxide, water, and dried over sodium sulfate. The crude oil (7 g) was purified by column chromatography (silica gel 230-400 mesh; 10/0 to 4/1 hexanes/EtOAc as eluent) to give pure 2-amino-N-(4-sec-butylphenyl)-benzamide as a brown solid. Yield: 1.8 g (27.3%).

Workup

customthe solvent was removed under reduced pressure
additionthe residue was diluted with ethyl acetate
washwashed with 1 N aqueous solution of sodium hydroxide, water
dry with materialdried over sodium sulfate
customThe crude oil (7 g) was purified by column chromatography (silica gel 230-400 mesh; 10/0 to 4/1 hexanes/EtOAc as eluent)

Sources & evidence

ORD record: ord-4df33a92f03240109a1b97594008ec40
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952021B2

Reaction notes

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