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

HRID 445436

반응식

HRID 445436 반응식
C([O-])(=O)C.[NH4+].[CH2:6]([O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22](=[O:24])[CH3:23])=[C:16]([N+:25]([O-])=O)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1>[Fe].O>[NH2:25][C:16]1[CH:15]=[C:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:19]([O:20][CH3:21])=[CH:18][C:17]=1[C:22](=[O:24])[CH3:23]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

생성물 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

A Mixture of iron powder (477 mmol, 27 g), ammonium acetate (500 mmol, 31.g), 1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-ethanone (120 mmol, 36 g), toluene (500 ml) and water (500 ml) was refluxed overnight, or until completion. The mixture was filtered through celite and washed with EtOAc. The organic layer washed with water and Sat. NaCl, dried over Na2SO4, and concentrated to afford the product, 90%. 1H NMR (CDCl3): 7.408-7.298 (5H, m), 7.130 (1H, s), 6.155 (2H, br), 6.104 (1H, s), 5.134 (2H, s), 3.834 (3H, s), 2.507 (3H, s). LC/MS (M+1=272).

후처리

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was filtered through celite
  3. washwashed with EtOAc
  4. washThe organic layer washed with water and Sat. NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the product, 90%

출처 및 근거

ORD 기록
ord-2ec2c040a76a4d408a6f9f4a6bfe50cb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476298B2

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