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

HRID 975937노트

반응식

HRID 975937 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-4965026ecec549299950638e6680434e
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610174

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