Hydrazine hydrate (1:1) → [trans-2-(4-Fluorophenyl)cyclopropyl]methanamine

HRID 1506158Notes

Reaction equation

HRID 1506158 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:4][CH:3]=1.O.NN>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH2:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 712582282-{[trans-2-(4-Fluorophenyl)cyclopropyl]methyl}isoindoline-1,3-dione

Product 1

HCID 68928221[trans-2-(4-Fluorophenyl)cyclopropyl]methanamineYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{[trans-2-(4-Fluorophenyl)cyclopropyl]methyl}isoindoline-1,3-dione (974 mg, 3.30 mmol) in ethanol (50 mL) was stirred with hydrazine monohydrate (825 mg, 16.5 mmol) at 100° C. for 30 minutes. The reaction mixture was concentrated to give the title compound as a colorless oil (360 mg, yield 66%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6e53660b5a5c4e2182568c47d109a5cc
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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