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

HRID 1676126Notes

Reaction equation

HRID 1676126 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.C(OCC)C>[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 is heated to 80° C. for 30 min in the microwave (300 W, active cooling during irradiation). The reaction mixture is diluted with diethyl ether and washed with water and brine. The organic extract is dried over Na2SO4, filtered and evaporated to give 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid (1.55 g) as a beige solid; 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. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f5d93b0e102948769986b271df6ca60a
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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