Nitric Acid → HCID 22180109, compound

HRID 495441Notes

Reaction equation

HRID 495441 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([F:15])[C:9]=1[F:16]>C(O)(=O)C>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[C:12]([N+:1]([O-:4])=[O:2])[C:11]([OH:14])=[C:10]([F:15])[C:9]=1[F:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22999141HCID 22999141, compound

Product 1

HCID 22180109HCID 22180109, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
45 °C

Procedure

Concentrated nitric acid (70% w/w) (0.72 mL, 11.2 mmol) in glacial acetic acid (2 mL) was added dropwise to a solution of 2,3-difluoro-4-hydroxy-benzoic acid methyl ester [Gonzales, Javier et al., PCT Int. Appl. (1999), 551 pp. WO 9901423 A1 19990114] (2 g, 10.6 mmol) in glacial acetic acid (28 mL). The mixture was stirred at 45° C. for 0.5 hour and then at room temperature overnight before it was evaporated to a quarter of the volume in vacuo. Water was added to the concentrate to give a solid precipitate which was filtered, washed with water twice and dried to give the title compound (2.2 g, 88%) as a colourless solid.

Workup

  1. customat room temperature overnight before it was evaporated to a quarter of the volume in vacuo
  2. additionWater was added to the
  3. concentrationconcentrate
  4. customto give a solid precipitate which
  5. filtrationwas filtered
  6. washwashed with water twice
  7. customdried

Sources & evidence

ORD record
ord-b589f0227792495082ea52d30c3da11f
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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