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

HRID 427609

反応式

HRID 427609 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-8c3d28d6a97640429c7e8a64d414bdb4
出典データセット
uspto-grants-2001_11
特許番号
US06313122B1

関連ノート

読み込み中…