Hydrazine → Benzenemethanamine, 4-chloro-3-fluoro-.alpha.-methyl-

HRID 1241479Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:9])=[CH:4][C:3]=1[F:21].NN>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][C:3]=1[F:21]

Participants

Conditions

Temperature: 80 °C

Procedure

2-[1-(4-Chloro-3-fluoro-phenyl)-ethyl]-isoindole-1,3-dione (4.08 g, 13.4 mmol) was dissolved in THF (100 mL). Hydrazine (4 mL) was added. The reaction was stirred at 80° C. for 1 h. Then, the solvent was evaporated and the crude was chromatograph over silica gel using ethyl acetate as solvent to yield 2.0 g of 1-(4-chloro-3-fluoro-phenyl)-ehtylamine. 1H NMR (400 Hz, Cl3CD) δ 7.34 (t, J=7.97 Hz, 1H), 7.18 (dd, J=1.90, 10.25 Hz, 1H), 7.08 (dd, J=1.90, 7.97 Hz, 1H), 4.12 (m, 1H), 1.36 (d, J=6.64, 3H).

Workup

customThen, the solvent was evaporated

Sources & evidence

ORD record: ord-a9535106fe67433db3186e51479f3118
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115598B2

Reaction notes

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