Water → 3-amino-5-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

HRID 432156Notes

Reaction equation

HRID 432156 reaction equation
[C:1]([C:3]([C:20]#[N:21])=[C:4](OC)[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)#[N:2].O.[NH2:23][NH2:24].O>C(O)C>[NH2:2][C:1]1[C:3]([C:20]#[N:21])=[C:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:6]=2)[NH:24][N:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 223472272-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile2×

Product 1

HCID 223467843-amino-5-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (Intermediate AA) (22.5 g) and 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene oil (15 g) were treated with a solution of 18 mL hydrazine hydrate in 25 mL ethanol and heated on the steambath for 1 hour, 15 mL ethanol added followed 10 mL water. The precipitated solid was collected and washed with 4:1 ethanol:water then dried in air giving 3-amino-4-cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid 30.0 g (80%) m.p. 187-188.5° C. 1H NMR (DMSO-d6,400 MHz) 12.11 (broad s, 1H), 7.80 (d, 2H), 7.42 (m, 2H), 7.18 (m, 1H), 7.09 (m, 4H), 6.47 (broad s, 2H). Calculated for C16H12N4O C 69.6H 4.3 N 20.3 Found C 69.5H 4.4 N 20.2.

Workup

  1. temperatureheated on the steambath for 1 hour
  2. customThe precipitated solid was collected
  3. washwashed with 4:1 ethanol
  4. dry with materialwater then dried in air

Sources & evidence

ORD record
ord-03a2a80fb72042cabb62d857e36f88e5
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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