P-Anisidine → 2-amino-N-(4-methoxyphenyl)benzamide

HRID 2228564Notes

Reaction equation

HRID 2228564 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:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)=[O:4]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 8359Isatoic Anhydride

Product 1

HCID 4788202-amino-N-(4-methoxyphenyl)benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of isatoic anhydride (4.894 g, 30 mmol), 4-methoxyaniline (3.695 g, 30 mmol) and toluene (60 mL) was heated to reflux for 5 h. After cooling, the reaction was filtered. The solid was triturated with CH2Cl2 (500 mL). This supernatant was combined with the above filtrate and concentrate. The residue was dissolved in CH2Cl2, decolorized with activated charcoal and crystallized from CH2Cl2/hexanes to give the title compound as a white solid (5.3 g, 73%); mp 116-7 C; MS(FD): 242.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling
  4. filtrationthe reaction was filtered
  5. customThe solid was triturated with CH2Cl2 (500 mL)
  6. concentrationconcentrate
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. customcrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-4c4d057741be4d209a313eb7da92dd5a
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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