4-Bromoaniline → 4-amino-N-(4-bromophenyl)-2-methoxy-5-nitrobenzamide

HRID 1410236Notes

Reaction equation

HRID 1410236 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:14][CH3:15])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Br:38][C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=1>CN(C=O)C>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH:43][C:42]2[CH:44]=[CH:45][C:39]([Br:38])=[CH:40][CH:41]=2)=[O:8])=[C:4]([O:14][CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 1010164-Amino-2-methoxy-5-nitrobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 595298014-amino-N-(4-bromophenyl)-2-methoxy-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound was prepared in accordance with the procedure in Example 59, step (a) using 4-amino-2-methoxy-5-nitrobenzoic acid (2.0 g; 9.43 mmol), TBTU (3.33 g; 10.4 mmol), TEA (2.9 mL; 20.8 mmol), 4-bromoaniline (1.62 g; 9.43 mmol) and DMF (70 mL). Yield: 3.41 g (99%).

Sources & evidence

ORD record
ord-ab75c8931ea84422b8d4b088babcb46d
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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