1-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one → 1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

HRID 909866ノート

反応式

HRID 909866 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:19][C:10]1[C:11]([OH:18])=[C:12]([C:15](=[O:17])[CH3:16])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 579889911-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one

生成物 1

HCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone収率 97.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

Zinc dust (5.5 g) was added portionwise to a suspension of 1-(4-(benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone (5.5 g) in acetic acid (55 mL) over 15 min, whilst maintaining the internal temperature below 40° C. with an ice bath. The mixture was allowed to attain ambient temperature and stirred for a further 2 h. The mixture was filtered through Celite (caution gets hot, do not allow to dry), washed with acetic acid, and the filtrate poured onto ice/water (500 mL). The resulting precipitate was filtered off, washed with water, and dried under vacuum at 40° C. to afford the subtitled compound as a light brown solid (4.8 g). 1H NMR (300 MHz, DMSO-d6) δ 7.53 (m, 2H), 7.48-7.33 (m, 3H), 7.28 (d, J=9.0 Hz, 1H), 6.72 (d, J=9.0 Hz, 1H), 5.29 (s, 2H), 2.59 (s, 3H).

後処理

  1. temperaturewhilst maintaining the internal temperature below 40° C. with an ice bath
  2. customto attain ambient temperature
  3. filtrationThe mixture was filtered through Celite (caution
  4. customto dry),
  5. washwashed with acetic acid
  6. additionthe filtrate poured onto ice/water (500 mL)
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with water
  9. customdried under vacuum at 40° C.

出典と根拠

ORDレコード
ord-a922e1c2bb5d47f1adccbf721ff18f8e
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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