Hydrochloric Acid → 2-Amino-1-(2,5-dimethoxyphenyl)ethan-1-ol

HRID 975937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975937
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([OH:14])[C:12]#[N:13].B.Cl>C1COCC1>[NH2:13][CH2:12][CH:11]([C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[OH:14]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 12216529α-Hydroxy-2,5-dimethoxybenzeneacetonitrile

Produkt 1

HCID 432602-Amino-1-(2,5-dimethoxyphenyl)ethan-1-olAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2.84 g (14.7 mmol) of (2, 5 dimethoxyphenyl)-hydroxy acetonitrile in 10 ml of dry THF was stirred and cooled using ice bath as a 1 M solution of borane in THF (90 mL) was added dropwise. After the addition was complete, the mixture was heated at reflux for 20 h. It was cooled and treated with 40 mL of 6N hydrochloric acid and washed with ethyl acetate. The aqueous layer was neutralized with 1N sodium hydroxide and extracted with ethyl acetate and concentrated to afford the desired compound as a white solid 1.5 g (52%). 1H NMR (300MHz, CDCl3) δ 6.97 (d, 1H, J=2.5 Hz), 6.73-6.69(m, 2H), 4.83-4.81(t, 1H, J=4.1 Hz), 3.72(s, 3H), 3.71(s, 3H), 2.89-2.65(m, 2H), 2.16(brs, 2H)

Aufarbeitung

  1. temperaturecooled
  2. additionwas added dropwise
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 20 h
  6. temperatureIt was cooled
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4965026ecec549299950638e6680434e
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610174

Notizen zur Reaktion

Wird geladen…