2-[(4-Methoxyphenyl)amino]benzoic acid → 2-Methoxy-9(10H)-acridone

HRID 1662935Notes

Reaction equation

HRID 1662935 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:9][C:10]3[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12](=[O:14])[C:7]=2[CH:8]=1

Participants

3

Reactant 1

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acid

Product 1

HCID 4070322-Methoxy-9(10H)-acridoneYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Polyphosphoric acid (50 gm) was heated to 160° C. under a nitrogen atmosphere. N-(4-methoxyphenyl)anthranilic acid (4.89 gm; 20 mmol) was added and the mixture stirred at 160° C. for 15 minutes. The reaction was cooled rapidly in an ice bath and water added to give a greenish yellow precipitate. This was filtered off, washed with water, then dilute sodium bicarbonate solution and again with water. The solid was finally dried at 50° C. under vacuum to give 3.67 gm (81%) of 2-methoxyacridone. δH (200 MHz, DMSO-d6) 3.86 (3H, s), 7.23 (1H, t), 7.55 (5H, m), 8.22 (1H, d), 11.7 (1H, s).

Workup

  1. temperatureThe reaction was cooled rapidly in an ice bath
  2. customto give a greenish yellow precipitate
  3. filtrationThis was filtered off
  4. washwashed with water
  5. customThe solid was finally dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-3663d04bce3742858fbf657503135bc9
Source dataset
uspto-grants-2011_10
Patent number
US08034558B2

Reaction notes

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