Acetic Acid → HCID 58964483, compound

HRID 2069204Notes

Reaction equation

HRID 2069204 reaction equation
[N+](=[CH:3][Si](C)(C)C)=[N-].[C:8]([NH:11][C:12]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([F:24])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:10])[CH3:9].C(O)(=O)C>CCCCCC.CO.C1C=CC=CC=1>[CH3:3][O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([F:24])[C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:12]=1[NH:11][C:8](=[O:10])[CH3:9]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 167693Trimethylsilyldiazomethane2×HCID 185367152-Acetamido-5-fluoro-4-nitrobenzoic acid

Product 1

HCID 58964483HCID 58964483, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

2.06 ml (4.12 mmol) of a 2M solution of diazomethyl-trimethyl-silane in hexane are added with slight cooling at 20° C. to a solution of 1.0 g (4.13 mmol) of 2-acetylamino-5-fluoro-4-nitro-benzoic acid in 15 ml of methanol and 35 ml of benzene. HPLC analysis after 15 minutes shows that there are still about 50% of the starting material present. Additional 2.4 ml (4.8 mmol) of the diazomethyl-trimethyl-silane solution are added. After standing for about 16 hours, no starting material can be detected by HPLC. 0.5 ml of glacial acetic acid are added and the reaction mixture is evaporated to dryness. Toluene is added and the mixture is again evaporated. The resulting residue is dissolved in refluxing ethyl acetate, hexane is added, the formed crystals are filtered, washed with hexane and dried at about 0.01 torr and 50° C. yielding 912 mg (86%) of 2-acetylamino-5-fluoro-4-nitro-benzoic acid methyl ester, m.p. 124-126° C.

Workup

  1. waitAfter standing for about 16 hours
  2. customthe reaction mixture is evaporated to dryness
  3. additionToluene is added
  4. customthe mixture is again evaporated
  5. dissolutionThe resulting residue is dissolved
  6. temperaturein refluxing ethyl acetate, hexane
  7. additionis added
  8. filtrationthe formed crystals are filtered
  9. washwashed with hexane
  10. customdried at about 0.01 torr and 50° C.

Sources & evidence

ORD record
ord-44674cc5b3724148b448848e016165ae
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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