Hydrazine hydrate (1:1) → 1-{[2-(Phenyloxy)phenyl]methyl}-1H-pyrazol-3-amine

HRID 1946333Notes

Reaction equation

[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH:19]=[CH:18][C:17]([N:20]3C(=O)C4C(=CC=CC=4)C3=O)=[N:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C1COCC1>[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH:19]=[CH:18][C:17]([NH2:20])=[N:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of crude 2-(1-{[2-(phenyloxy)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (2.35 g, 5.94 mmol) in THF (30 ml) was added hydrazine hydrate (1.44 ml, 29.7 mmol, Aldrich). The resulting colourless solution was stirred at 50° C. for 2 h. A white solid precipitated. The suspension was cooled to ambient temperature and filtered through a sinter funnel. The filtrate was then filtered through a hydrophobic frit and concentrated under reduced pressure to give the title compound as a white solid (1.58 g); LCMS: (System 3) MH+=266, tRET=0.86 min.

Workup

customA white solid precipitated
temperatureThe suspension was cooled to ambient temperature
filtrationfiltered through a sinter funnel
filtrationThe filtrate was then filtered through a hydrophobic frit
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0c01ab446aa74ea0bfadd433178adf1a
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

Loading…