3'-Nitro-4'-methylacetophenone → 1-(3-Amino-4-methylphenyl)ethan-1-ol

HRID 1019075

반응식

HRID 1019075 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-])=O.[BH4-].[Na+].[H][H]>CO.C(OCC)(=O)C.[Pd]>[OH:9][CH:8]([C:5]1[CH:4]=[C:3]([C:2]([CH3:1])=[CH:7][CH:6]=1)[NH2:11])[CH3:10]

참가 물질

7

반응물 3

HCID 792463'-Nitro-4'-methylacetophenoneHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 120512021-(3-Amino-4-methylphenyl)ethan-1-ol

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To an ice-cold solution of 4-methyl-3-nitroacetophenone (25 g, 139 mmol) in methanol (200 mL) is added sodium borohydride (6.2 g, 163 mmol) over 15 minutes. The mixture is stirred at room temperature for 1 hour, then is quenched with water. The mixture is rotary evaporated and the residue is partitioned between water and ethyl acetate. The organic layer is dried (magnesium sulfate) and rotary evaporated to afford a light brown viscous oil. The oil is diluted with ethyl acetate (200 mL), 5% palladium-on-carbon (5 g) is added and the mixture is treated with hydrogen at 40 psi for 18 hours. The mixture is then filtered on Celite and the filtrate is rotary evaporated to afford 3-(1-hydroxyethyl)-6-methylaniline as a light yellow, pasty solid.

후처리

  1. customis quenched with water
  2. customThe mixture is rotary evaporated
  3. customthe residue is partitioned between water and ethyl acetate
  4. dry with materialThe organic layer is dried (magnesium sulfate)
  5. customrotary evaporated
  6. customto afford a light brown viscous oil
  7. additionis added
  8. filtrationThe mixture is then filtered on Celite
  9. customthe filtrate is rotary evaporated

출처 및 근거

ORD 기록
ord-d55df7e059594cfc98560ab9442fa27c
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486190B1

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