P-Anisidine → 2-Amino-N-(4-methoxyphenyl)-4-nitrobenzamide

HRID 395719

Reaction equation

HRID 395719 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[NH:12]C(=O)[O:10][C:8](=O)[C:7]2=[CH:14][CH:15]=1)([O-:3])=[O:2].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1>CN(C)C=O>[NH2:12][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]=1[C:8]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)=[O:10]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 2820894-Nitro-isatoic anhydride

Product 1

HCID 105173792-Amino-N-(4-methoxyphenyl)-4-nitrobenzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-nitroisatoic anhydride (2.08 g, 10.0 mmol) and p-anisidine (1.35 g, 11.0 mmol) in N,N-dimethylformamide (10 mL) was heated at 80° C. for 2.5 h. After cooling, the reaction was poured into ice cold 3 N hydrochloric acid (60 mL). The resulting solid was filtered and washed with 1 N hydrochloric acid and water. Drying in vacuo gave 2.73 g (95%) of the title compound as a greenish yellow solid; mp 193-7° C.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting solid was filtered
  3. washwashed with 1 N hydrochloric acid and water
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-490fd889391e46b88fe83968a6b11759
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Linked notes

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