Water → 5-amino-3-(3-ethoxy-4-methoxyphenyl)-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile

HRID 238064Notes

Reaction equation

HRID 238064 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12](OC)=[C:13]([C:16]#[N:17])[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[OH:20][CH2:21][CH2:22][NH:23][NH2:24].C(N(CC)CC)C.O>C(O)C>[NH2:17][C:16]1[N:23]([CH2:22][CH2:21][OH:20])[N:24]=[C:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[C:13]=1[C:14]#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 80172-HydrazinoethanolHCID 8471TriethylamineHCID 866170192-((3-Ethoxy-4-methoxyphenyl)(methoxy)methylene)malononitrile

Product 1

HCID 687075235-amino-3-(3-ethoxy-4-methoxyphenyl)-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-((3-ethoxy-4-methoxyphenyl)(methoxy)methylene)malononitrile (200 mg, 0.78 mmol), 2-hydroxyethylhydrazine (0.056 mL, 0.78 mmol), and triethylamine (0.10 mL, 0.78 mmol) were combined in ethanol (5 mL) and heated to reflux for 90 minutes. The reaction was then cooled to RT, water was added and the aqueous phase was extracted three times with EtOAc, CH2Cl2, and CHCl3. The organic phase was concentrated and carried onto the next step without further characterization. ESI-MS (M+H)+ m/z calcd 303.1, found 303.0.

Workup

  1. temperatureheated
  2. temperatureto reflux for 90 minutes
  3. extractionthe aqueous phase was extracted three times with EtOAc, CH2Cl2, and CHCl3
  4. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-5380aed4bd6747a9a533c7121ce7afd1
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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