Hydrazine hydrate (1:1) → HCID 178509389, compound

HRID 64256

Reaction equation

HRID 64256 reaction equation
CO[C:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)=[C:4]([C:7]#[N:8])[C:5]#[N:6].O.[NH2:23][NH2:24]>C(O)C>[NH2:6][C:5]1[NH:24][N:23]=[C:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[C:4]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 223472272-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile

Product 1

HCID 178509389HCID 178509389, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile (80 g, 290 mmol) in ethanol (200 mL) was added hydrazine hydrate (20 mL). The mixture was stirred at RT for 16 hr then was concentrated to give the crude product and washed with MeOH (30 mL) to afford 55 g (68.8%) of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile as a off-white solid. 1H NMR (DMSO-d6) δ 12.11 (br s, 1H), 7.80 (d, J=8.8 Hz, 2H), 7.46-7.39 (m, 2H), 7.18 (t, J=7.6 Hz, 1H), 7.12-7.04 (m, 4H), 6.43 (br s, 2H).

Workup

  1. concentrationthen was concentrated
  2. customto give the crude product
  3. washwashed with MeOH (30 mL)

Sources & evidence

ORD record
ord-2b70bc0aa45e45eabbf68769fb969725
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Linked notes

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