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

HRID 1665919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665919
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 574374143-(4-Cyano-2-ethyl-6-methylphenyl)propionic acidAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. washwashed with water and brine
  2. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-973f26b4c4f4447196c6a71e93615c76
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039644B2

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