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

HRID 385144Notes

Reaction equation

HRID 385144 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7])=O.Cl.[NH2:20]O>C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7])#[N:20]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866681823-Formyl-4-methoxy-5-trifluoromethoxybenzoic acid

Product 1

HCID 681091153-Cyano-4-methoxy-5-trifluoromethoxybenzoic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

3-formyl-4-methoxy-5-trifluoromethoxybenzoic acid (4.22 g) was dissolved in formic acid (20 mL), and hydroxylamine hydrochloride (1.22 g) was added to the solution, and then the mixture was refluxed for 16 hours. The solvent was distilled off under reduced pressure and 1N hydrochloric acid 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 (3.97 g) as a brown solid.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. distillationThe solvent was distilled off under reduced pressure and 1N hydrochloric acid
  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-ee7ce77016534c12a0ed65ed14c712b4
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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