1-(4-Cyclohexyl-3-nitrophenyl)ethanone → 1-(3-Amino-4-cyclohexylphenyl)ethanone

HRID 1777330Notes

Reaction equation

HRID 1777330 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=2[N+:16]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[NH2:16][C:8]1[CH:9]=[C:10]([C:13](=[O:15])[CH3:14])[CH:11]=[CH:12][C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 219966001-(4-Cyclohexyl-3-nitrophenyl)ethanone

Product 1

HCID 234649641-(3-Amino-4-cyclohexylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Stannous chloride dihydrate (15.8 g, 0.07 mol) is added to a solution of 1-(4-cyclohexyl-3-nitrophenyl)ethanone (5.8 g, 0.0235 mol) in concentrated hydrochloric acid (35 mL) at 0-5° C. The reaction mixture is slowly brought to 60-65° C. and is stirred at this temperature for 15 minutes. After cooling to room temperature the reaction mixture is extracted with ethyl acetate (3×100 mL). The pH is adjusted to 8.0-9.0 using solid sodium bicarbonate. After washing with water (1×15 mL) the organic layer is dried over sodium sulfate and concentrated under reduced pressure to yield the crude, which is purified by column chromatography (230-400 mesh; ethyl acetate:n-hexane, 3:7) to give 1-(3-amino-4-cyclohexylphenyl)ethanone.

Workup

  1. customis slowly brought to 60-65° C.
  2. extractionis extracted with ethyl acetate (3×100 mL)
  3. washAfter washing with water (1×15 mL) the organic layer
  4. dry with materialis dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield the crude, which
  7. customis purified by column chromatography (230-400 mesh; ethyl acetate:n-hexane, 3:7)

Sources & evidence

ORD record
ord-7dacc30332094f7d89ca08785337d023
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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