Hydrazine hydrate (1:1) → (E)-3-(3,5-difluoro-4-phenoxyphenyl)-2-methylprop-2-en-1-amine

HRID 1470142Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](/[CH:16]=[C:17](\[CH3:30])/[CH2:18][N:19]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[C:6]([F:15])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.NN>CO>[F:1][C:2]1[CH:3]=[C:4](/[CH:16]=[C:17](\[CH3:30])/[CH2:18][NH2:19])[CH:5]=[C:6]([F:15])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (E)-2-(3-(3,5-difluoro-4-phenoxyphenyl)-2-methylallyl)isoindoline-1,3-dione (Intermediate 93.2, 100 mg, 0.25 mmol) in methanol (1 mL) was added hydrazine hydrate (25 mg, 0.5 mmol) and the reaction stirred at 50° C. overnight. The white solid was filtered with DCM, and the solvent removed from the filtrate. The residue was brought up in DCM and filtered. This was repeated until no further precipitate formed to give 49.5 mg of the title compound (71%) as a yellow oil, a 10 mg portion of which was diluted with 1N HCl and freeze dried to give 7.8 mg of the title compound as an HCl salt. 1H-NMR (400 MHz, d6-DMSO): δ 8.25 (s, 2H), 7.37 (t, 2H), 7.20 (d, 2H), 7.12 (t, 1H), 6.97 (s, 1H), 3.57 (s, 2H), 1.96 (s, 3H). MS (m/z): 258.96 (M-NH2).

Workup

filtrationThe white solid was filtered with DCM
customthe solvent removed from the filtrate
filtrationfiltered
customformed

Sources & evidence

ORD record: ord-c924aff9f87e4b36b97d3132fb9a7122
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006281B2

Reaction notes

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