Ethanol → HCID 178488694, compound

HRID 1452756Notes

Reaction equation

CO[C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]#[N:12])=[CH:5][CH:4]=1.[OH2:14].[NH2:15][NH2:16].[CH2:17](O)C>>[NH2:12][C:11]1[NH:16][N:15]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:14][CH3:17])=[CH:4][CH:5]=2)[CH:10]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 24654Hydrazine hydrate (1:1)

HCID 2333984-Methoxybenzoylacetonitrile

Product 1

HCID 178488694HCID 178488694, compoundYield 97%

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(4-methoxyphenyl)-3-oxo-propionitrile (2.0 g, 11.4 mmol) in absolute ethanol (21 mL) was added hydrazine hydrate (3.32 mL, 68.3 mmol). The reaction mixture was stirred at 80° C. for 15 hours, then it was concentrated in vacuo and purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to give 2.02 g (97% yield) of 5-amino-3-(4-methoxyphenyl)pyrazole as a white solid. 1H NMR (d6-DMSO) δ: 11.69 (s, 1H), 7.55 (d, 2H), 6.92 (d, 2H), 5.66 (s, 1H), 4.62 (broad s, 2H), 3.75 (s, 3H); HPLC/MS m/z: 190.1 [MH]+.

Workup

concentrationit was concentrated in vacuo
custompurified on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record: ord-ed166620a1d7408e8994f7f8f785ec80
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473783B2

Reaction notes

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