Hydrazine → (5-Phenylthiophen-3-yl)methanamine

HRID 915696Notes

Reaction equation

HRID 915696 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[C:9]([CH2:12][N:13]3C(=O)C4C(=CC=CC=4)C3=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>CO>[C:1]1([C:7]2[S:11][CH:10]=[C:9]([CH2:12][NH2:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 691299712-(5-Phenylthiophen-3-ylmethyl)isoindole-1,3-dione

Product 1

HCID 69129967(5-Phenylthiophen-3-yl)methanamineYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepare a solution of 2-(5-phenylthiophen-3-ylmethyl)isoindole-1,3-dione (565 mg, 1.77 mmol) in methanol (57 mL). Add hydrazine (0.35 mL, 11.14 mmol). Heat the mixture to reflux. After stirring for 1 hour, cool the mixture to room temperature and concentrate. Perform flash chromatography on silica gel eluting with 50:40:9:1 methylene chloride/CHCl3/MeOH/concentrated NH4OH to afford 280 mg of the title compound as a yellow solid. MS: m/e=190 [MH+].

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-451f52bb10c94aa1b150746b25abd3d0
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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