4-Chloroaniline → 3-Amino-4-methoxy-N-(4-chlorophenyl)-benzamide

HRID 1859646Notes

Reaction equation

HRID 1859646 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[N+:18]([O-])=O.[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>CN(C)C=O>[NH2:18][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[O:8][CH3:7])[C:13]([NH:26][C:25]1[CH:27]=[CH:28][C:22]([Cl:21])=[CH:23][CH:24]=1)=[O:15]

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 65578Oxalyl chlorideHCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 167929923-Amino-4-methoxy-N-(4-chlorophenyl)-benzamideYield 27.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (5.5 mL, 63.05 mmol), 4-methoxy-3-nitrobenzoic acid (11.30 g, 57.32 mmol), dimethylformamide (1.0 mL, 1.29 mmol), and 4-chloroaniline (14.6 g, 114 mmol) to afford the product (4.4 g); m.p. 191-192° C.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9dc6702361c14a57a21251e68234bb2a
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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