Hydroxyamine hydrochloride → 3-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid

HRID 1958775Notes

Reaction equation

HRID 1958775 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[C:5]([CH3:11])[C:4]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:2].Cl.[NH2:18]O>CN1CCCC1=O.CCOCC>[C:9]([C:7]1[CH:6]=[C:5]([CH3:11])[C:4]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:3]([CH2:1][CH3:2])[CH:8]=1)#[N:18]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 574374063-(2-Ethyl-4-formyl-6-methylphenyl)propionic acid

Product 1

HCID 574374143-(4-Cyano-2-ethyl-6-methylphenyl)propionic acidYield 94.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-(2-ethyl-4-formyl-6-methyl-phenyl)-propionic acid (1.67 g, 7.58 mmol) and hydroxylamine hydrochloride (780 mg, 11.36 mmol) in 1-methyl-2-pyrrolidone was heated to 80° C. for 30 min in the microwave (300 W, active cooling during irradiation). The reaction mixture was diluted with Et2O and washed with water and brine. The org. extract was dried over Na2SO4, filtered and evaporated to give 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid as a beige solid (1.55 g). LC-MS: tR=0.89 min, 1H NMR (D6-DMSO): δ 12.25 (s, 1H), 7.45 (s, 2H), 2.91-2.84 (m, 2H), 2.67-2.59 (m, 2H), 2.35-2.30 (m, 5H), 1.14 (t, J=7.6 Hz, 3H).

Workup

  1. washwashed with water and brine
  2. extractionextract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a6cb1b98a52346d9b15f1941909f3ba0
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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