Diethyl Ether → 5-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

HRID 1434534

Reaction equation

HRID 1434534 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.C(N(CC)CC)C.C(OCC)C>C(O)C>[NH2:20][C:19]1[N:10]([C:4]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=2[CH3:2])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 124050102,6-Dimethylphenylhydrazine hydrochloride

Product 1

HCID 121505545-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.0 g (17.3 mmol) of 2,6-dimethylphenylhydrazine hydrochloride are suspended with 2.1 g (17.3 mmol) of ethoxymethylenemalononitrile in 40 ml of ethanol, and 7.3 ml (52.1 mmol) of triethylamine are added. The reaction mixture is heated to reflux for 3 h, during which a clear solution forms. After cooling to room temperature, diethyl ether is added to this. The triethyl-ammonium chloride which precipitates is filtered off. The solvent is removed in vacuo, and the residue is purified by preparative HPLC (YMC gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 2.3 g (62% of theory) of the product are obtained as yellow crystals.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 3 h, during which a clear solution forms
  4. customThe triethyl-ammonium chloride which precipitates
  5. filtrationis filtered off
  6. customThe solvent is removed in vacuo
  7. customthe residue is purified by preparative HPLC (YMC gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  8. custom2.3 g (62% of theory) of the product are obtained as yellow crystals

Sources & evidence

ORD record
ord-44edd7f0bc4c422c98feb6d372956a56
Source dataset
uspto-grants-2009_11
Patent number
US07615558B2

Linked notes

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