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

HRID 1019075

反応式

HRID 1019075 の反応式
[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]

参加物

7

反応物 3

HCID 792463'-Nitro-4'-methylacetophenoneHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d55df7e059594cfc98560ab9442fa27c
出典データセット
uspto-grants-2002_11
特許番号
US06486190B1

関連ノート

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