Sodium borohydride → 3-Benzyloxy-4-methyl-phenylamine

HRID 395758

反応式

HRID 395758 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.CO.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[CH3:15])[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 4311764Sodium borohydrideHCID 181745022-Benzyloxy-1-methyl-4-nitro-benzene

生成物 1

HCID 27946253-Benzyloxy-4-methyl-phenylamine収率 97%

試薬・触媒・溶媒 3

HCID 62601Nickel acetate tetrahydrate触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-benzyloxy-4-methylnitrobenzene (1.1 g, 4.4 mmol) in tetrahydrofuran (25 mL) and methanol (50 mL) was added nickel acetate tetrahydrate (2.2 g, 8.7 mmol). The solution was cooled to 0° C. and sodium borohydride (0.66 g, 17.4 mmol) was added in small portions. After gas evolution had ceased, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate and concentrated ammonium hydroxide. The layers were separated and the organic phase was washed with ammonium hydroxide followed by saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated In vacuo to give 0.9 g (97%) of the title product as an off-white solid.

後処理

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and concentrated ammonium hydroxide
  3. customThe layers were separated
  4. washthe organic phase was washed with ammonium hydroxide
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated In vacuo

出典と根拠

ORDレコード
ord-45acb0023692450f80e5692efd70658b
出典データセット
uspto-grants-2003_08
特許番号
US06605626B2

関連ノート

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