Reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:12]([OH:14])=[O:13])(=[O:7])[CH3:6].NC1C([N+]([O-])=O)=C(C)C([N+]([O-])=O)=CC=1C#N>>[C:5]([NH:8][C:9]1[C:10]([N+:1]([O-:4])=[O:2])=[C:11]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:12]([OH:14])=[O:13])(=[O:7])[CH3:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
Fuming nitric acid (100 mL, 2.4 mol) is cooled to about 0° C. (ice/acetone/water bath) and 3-(Acetylamino)-4-methylbenzoic Acid (14) (24.567 g, 127.2 mmol) is added in small portions over about 30 minutes, at rate to maintain the internal reaction temperature <5° C. The hetereogeneous reaction mixture is then stirred at about 0° C. for an additional 1 hour. The reaction mixture is then added to ice water (300 mL) and stirred for about 1 hour. The solid obtained is filtered and dried to provide a mixture of 3-N-acetyl-4-methyl-2-nitro benzoic acid (5) and 3-N-acetyl-4-methyl-5-nitro benzoic acid, in ratio of about 78:22 (27.79 g, 92% Combined Yield). A portion of this mixture (23.458 g) is recrystallized from acetic acid (300 mL) to give 3-(Acetylamino)-4-methyl-2-nitrobenzoic Acid (15), as a white solid (15.370 g, 51% yield).
Workup
- additionis added in small portions over about 30 minutes, at rate
- temperatureto maintain the internal reaction temperature <5° C
- stirringstirred for about 1 hour
- customThe solid obtained
- filtrationis filtered
- customdried
- customto provide
- customin ratio of about 78:22 (27.79 g, 92% Combined Yield)
- customA portion of this mixture (23.458 g) is recrystallized from acetic acid (300 mL)
Sources & evidence
- ORD record
- ord-bbcd564821964a078314caf03b648d3a
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07304084B2
Linked notes
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