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

HRID 975937ノート

反応式

HRID 975937 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-4965026ecec549299950638e6680434e
出典データセット
uspto-grants-1997_03
特許番号
US05610174

反応ノート

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