Hydroxyamine hydrochloride → 3-Cyano-4-methoxy-5-trifluoromethylbenzoic acid

HRID 385015Notes

Reaction equation

HRID 385015 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7])=O.Cl.[NH2:19]O>C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7])#[N:19]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866681493-Formyl-4-methoxy-5-trifluoromethylbenzoic acid

Product 1

HCID 681090843-Cyano-4-methoxy-5-trifluoromethylbenzoic acidYield 27.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

3-formyl-4-methoxy-5-trifluoromethylbenzoic acid (58.04 g) was dissolved in formic acid (290 mL), and hydroxylamine hydrochloride (17.07 g) was added to the solution, and the mixture was refluxed for 19 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (15.62 g) as a brown solid.

Workup

  1. temperaturethe mixture was refluxed for 19 hours
  2. distillationThe solvent was distilled off under reduced pressure and water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-15ad05f8247b401985f50d789c585960
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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