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

HRID 427609

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HRID 427609 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 27946253-Benzyloxy-4-methyl-phenylamine수율 97%

시약·촉매·용매 3

HCID 62601Nickel acetate tetrahydrate촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8c3d28d6a97640429c7e8a64d414bdb4
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313122B1

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