Methanol → 4-(4-Chlorophenyl)but-3-yn-2-amine

HRID 597886Notes

Reaction equation

HRID 597886 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:10]([N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:11])=[CH:4][CH:3]=1.CO.NN>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH:10]([NH2:12])[CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 573568212-[4-(4-Chlorophenyl)but-3-yn-2-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 158410294-(4-Chlorophenyl)but-3-yn-2-amineYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[3-(4-chloro-phenyl)-1-methyl-prop-2-ynyl]-isoindole-1,3-dione (4.1 g, 13.2 mmol) in 20 mL of dichloromethane was added 30 mL of methanol followed by hydrazine (4.2 mL, 133 mmol, 10 eq.). The mixture was stirred for 1 hr, filtered, concentrated and chromatographed with 3% methanol-dichloromethane to provide 1.5 g of 3-(4-chloro-phenyl)-1-methyl-prop-2-ynylamine.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customchromatographed with 3% methanol-dichloromethane

Sources & evidence

ORD record
ord-900f6bb4da1d496db81b32fb449c4fb2
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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