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

HRID 427560Notes

Reaction equation

HRID 427560 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:20]=[CH:19][C:18]([NH2:21])=[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:21][C:18]1[CH:19]=[CH:20][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 (4.9 g, 30 mmol) and p-anisidine (3.7 g, 30 mmol) in toluene (60 mL) was heated to reflux for 5 h. After cooling, the supernatant was decanted and the solid was suspended in methylene chloride (500 mL). The resulting suspension was filtered. The filtrate was combined with the supernatant from above, partially concentrated, diluted with hexane, and decolorized with charcoal. The resulting crystallization provided 5.3 g (73%) of the title compound as a white solid; mp 116-7° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling
  4. customthe supernatant was decanted
  5. filtrationThe resulting suspension was filtered
  6. concentrationpartially concentrated
  7. additiondiluted with hexane
  8. customThe resulting crystallization

Sources & evidence

ORD record
ord-92ed8df664334c3ea3ffb198dba81512
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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