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

HRID 1856546Notes

Reaction equation

HRID 1856546 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>[CH3:3][C:2]([OH:15])([C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1)[CH3:1]

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

20 grams of 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol in 250 grams of isopropanol was hydrogenated in the presence of a cobalt polysulfide paste prepared as above for 1.25 hours at 110° C. and 1000 psig (6.9 MPa) of hydrogen pressure. After filtration, and evaporation of the solvent, the residue was crystallized from toluene to give 13.1 grams (77% yield, recovered) of 2-methyl-4-(3-aminophenyl)-3-butyn-2-ol, melting point 117° to 120° C.

Workup

  1. filtrationAfter filtration, and evaporation of the solvent
  2. customthe residue was crystallized from toluene

Sources & evidence

ORD record
ord-164f6727972f47cda6e30335aa45149d
Source dataset
uspto-grants-1980_08
Patent number
US04219679

Reaction notes

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