Toluene → 1-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

HRID 445467

반응식

HRID 445467 반응식
C([O-])=O.[NH4+].[CH2:5]([O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21](=[O:23])[CH3:22])=[C:15]([N+:24]([O-])=O)[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(C)C=CC=CC=1>[Fe].O>[NH2:24][C:15]1[CH:14]=[C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:18]([O:19][CH3:20])=[CH:17][C:16]=1[C:21](=[O:23])[CH3:22]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 2723923Ammonium formateHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

생성물 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone수율 90%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

A mixture of iron powder (27 g, 0.48 g atoms), ammonium formate (31 g, 500 mmol), 1-(4-benzyloxy-5-methoxy-2-nitrophenyl)ethanone (36 g, 120 mmol), toluene (500 mL) and water (500 mL) was heated to reflux overnight. The mixture was filtered through celite and washed with ethyl acetate. The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4 and concentrated to afford 1-(2-amino-4-benzyloxy-5-methoxyphenyl)ethanone (29.3 g, 90%). 1H NMR (CDCl3): δ 7.41-7.30 (m, 5H), 7.13 (s, 1H), 6.16 (br s, 2H), 6.10 (s, 1H), 5.13 (s, 2H), 3.83 (s, 3H), 2.51 (s, 3H). LC/MS (M+H=272).

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered through celite
  4. washwashed with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-be703c2cc0ec44b18e90bb9c23cd29eb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476298B2

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