Anthranilamide → 2-(4-Cyanophenylamino)Benzamide

HRID 1354970Notes

Reaction equation

HRID 1354970 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH2:15])=[O:14].CCCCCC>C(OCC)(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([NH2:15])=[O:14])=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 8058HexaneHCID 12162Benzonitrile, 4-bromo-

Product 1

HCID 211061232-(4-Cyanophenylamino)BenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the general procedure, 4-bromobenzonitrile (91 mg, 0.5 mmol) was coupled with 2-aminobenzamide (102 mg, 0.75 mmol) with the reaction time of 17 h. Chromatography on silica gel column with 1:1 hexane:ethyl acetate gave 103 mg (87%) of the title compound as a pale yellow solid.

Sources & evidence

ORD record
ord-d59c3353d4a04c52930797418b77a83c
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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