Isatoic Anhydride → 2-amino-N-(3-methoxyphenyl)benzamide

HRID 1614206Notes

Reaction equation

HRID 1614206 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>C(Cl)Cl>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([O:14][CH3:13])[CH:16]=1)=[O:4]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 108243-Methoxyaniline

Product 1

HCID 24422032-amino-N-(3-methoxyphenyl)benzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

Isatoic anhydride (32.63 g, 200 mmol) and 3-methoxyaniline (24.63 g, 200 mmol) were combined neat and heated at 120° C. for 2 hours. The reaction product was taken up in methylene chloride and chromatographed (20% ethyl acetate/hexanes, SiO2), to provide 38.75 g (80%) of 2-amino-N-(3-methoxyphenyl)benzamide. An analytical sample was obtained by recrystallization from ethyl acetate: mp 75°-77° C.

Workup

  1. customchromatographed (20% ethyl acetate/hexanes, SiO2)

Sources & evidence

ORD record
ord-8f0d676e513b4f0b8b9bb609abfbf548
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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