Acetic Acid → HCID 58964477, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8](F)[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[NH:14][C:15](=[O:17])[CH3:16].C[O-].[Na+].[C:22](O)(=[O:24])C.C(OCC)(=O)C>CO.O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([O:24][CH3:22])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[NH:14][C:15](=[O:17])[CH3:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
256 mg (1.0 mmol) of 2-acetylamino-5-fluoro-4-nitro-benzoic acid methyl ester are dissolved in 5.1 ml of refluxing methanol abs. and cooled to 23° C. whereby some of the material recrystallizes. 81 mg (1.5 mmol) of sodium methanolate are added and the mixture is stirred under argon at room temperature for 16 hours. Acetic acid is added until a pH value of 5 is reached, the resulting mixture is distributed between ethyl acetate and water, the organic phase is separated, washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue is chromatographed on 100 g of silica gel (0.04-063 mm) with toluene-ethyl acetate (3:1), fraction size 12 ml. The fractions 37-46 are combined and evaporated, yielding 77 mg (28%) of 2-acetylamino-5-methoxy-4-nitro-benzoic acid methyl ester as yellowish crystals, m.p. 141-143° C.
Workup
- customrecrystallizes
- customthe organic phase is separated
- washwashed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
- customThe residue is chromatographed on 100 g of silica gel (0.04-063 mm) with toluene-ethyl acetate (3:1), fraction size 12 ml
- customevaporated
Sources & evidence
- ORD record
- ord-e23f212de2754cf292c7357d8608ee22
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299085B2
Reaction notes
Loading…