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

HRID 395758

반응식

HRID 395758 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

반응 조건

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-45acb0023692450f80e5692efd70658b
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605626B2

연결된 노트

불러오는 중…