Sodium Carbonate → ETHYL 5-AMINO-1-(4-METHOXYPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE

HRID 1518309Notes

Reaction equation

HRID 1518309 reaction equation
[C:1](/[C:3](=[CH:9]/OCC)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Cl.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[NH2:2][C:1]1[N:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[N:23]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1550346Ethyl ethoxymethylenecyanoacetateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 4456866ETHYL 5-AMINO-1-(4-METHOXYPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (Z)-ethyl 2-cyano-3-ethoxyacrylate (9.64 g, 57.0 mmol), 4-methoxyphenylhydrazine hydrochloride (9.95 g, 57.0 mmol) and Na2CO3 (6.04 g, 57.0 mmol) in EtOH (480 mL) was refluxed for 5 h and stirred overnight at rt. The insoluble material was filtered off and the filtrate was concentrated and solid precipitated. The precipitate was collected and washed with MeOH and washed with water extensively. The pale solid was dried to provide the desired product: 1H NMR (400 MHz, DMSO-D6) δ ppm 7.65 (1H, s), 7.42 (2H, d), 7.07 (2H, d), 6.15 (2H, s), 4.14-4.26 (2H, m), 3.81 (3H, s), 1.27 (3H, t).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. customsolid precipitated
  5. customThe precipitate was collected
  6. washwashed with MeOH
  7. washwashed with water extensively
  8. customThe pale solid was dried

Sources & evidence

ORD record
ord-deaa8b7154ef42e49d5d3ac4e932beee
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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