Hydroxyamine hydrochloride → 3-Cyano-5-cyclobutyl-4-methoxybenzoic acid

HRID 385051Notes

Reaction equation

HRID 385051 reaction equation
[CH:1]1([C:5]2[CH:6]=[C:7]([CH:11]=[C:12]([CH:16]=O)[C:13]=2[O:14][CH3:15])[C:8]([OH:10])=[O:9])[CH2:4][CH2:3][CH2:2]1.Cl.[NH2:19]O>C(O)=O>[C:16]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])#[N:19]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866681583-Cyclobutyl-5-formyl-4-methoxybenzoic acid

Product 1

HCID 681083433-Cyano-5-cyclobutyl-4-methoxybenzoic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

3-cyclobutyl-5-formyl-4-methoxybenzoic acid (458 mg) was dissolved in formic acid (2.5 mL), and hydroxylamine hydrochloride (163 mg) was added to the solution, and then 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 (404 mg) 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-8583e1039c9a49308f8b2e748e4f605a
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

Loading…