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

HRID 445436

反応式

HRID 445436 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-2ec2c040a76a4d408a6f9f4a6bfe50cb
出典データセット
uspto-grants-2013_07
特許番号
US08476298B2

関連ノート

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