3-Butyn-2-ol, 2-methyl-4-(3-nitrophenyl)- → 3-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-

HRID 1913856Notes

Reaction equation

HRID 1913856 reaction equation
[CH3:1][C:2]([OH:15])([C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)[CH3:3].[H][H]>C(O)(C)C>[NH2:12][C:8]1[CH:7]=[C:6]([C:5]#[C:4][C:2]([CH3:3])([OH:15])[CH3:1])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1184803-Butyn-2-ol, 2-methyl-4-(3-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 1122363-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-Yield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In an autoclave there are introduced—under nitrogen atmosphere—20.0 g of 2-methyl-4-(3-nitrophenyl)but-3-yn-2-ol and 300 mL of Isopropanol and 1.0 g of cobalt polysulfide paste (see U.S. Pat. No. 4,219,679A1). The mixture was hydrogenated for 1 hr and 15 minutes at 110° C. and 1000 psig of hydrogen pressure. After removing the catalyst by filtering, the solution was concentrated to dryness and the residue was crystallised from Toluene providing 13.1 g of the product of formula (IV) for a molar yield of 77%.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtering
  3. concentrationthe solution was concentrated to dryness
  4. customthe residue was crystallised from Toluene providing 13.1 g of the product of formula (IV) for a molar yield of 77%

Sources & evidence

ORD record
ord-722ef5b3b69a497587a257c4cfcd939d
Source dataset
uspto-grants-2013_12
Patent number
US08609841B2

Reaction notes

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