1,3-Dimethyl-1H-pyrazol-5-amine → HCID 136404513, compound

HRID 1031523Notes

Reaction equation

HRID 1031523 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH3:8])=[N:3]1.[CH3:9][O:10][C:11](=[O:26])[C:12](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)[C:13]([CH3:15])=O>C(O)C>[CH3:9][O:10][C:11]([C:12]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:5]2[C:4]([CH3:8])=[N:3][N:2]([CH3:1])[C:6]=2[NH:7][C:13]=1[CH3:15])=[O:26]

Participants

4

Reactant 2

HCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 1536427Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoate

Product 1

HCID 136404513HCID 136404513, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-Dimethyl-5-pyrazolamine (3.33 g; 0.030 mol) is dissolved in ethanol (35 ml) and methyl-2-(3-nitrobenzyliden)acetoacetate (6.75 g; 0.27 mol) is added thereto. The mixture is refluxed for about 5 hours, then the solvent is evaporated under reduced pressure and the residue is taken up in methylene chloride, washed with 2% hydrochloric acid and then with saturated aqueous sodium bicarbonate, the organic phase is dried over sodium sulphate and then the solvent is evaporated. The solid compound of the title is recovered by filtration, after taking up in ethyl ether. M.p. 163°-166° C.

Workup

  1. temperatureThe mixture is refluxed for about 5 hours
  2. customthe solvent is evaporated under reduced pressure
  3. washwashed with 2% hydrochloric acid
  4. dry with materialwith saturated aqueous sodium bicarbonate, the organic phase is dried over sodium sulphate
  5. customthe solvent is evaporated
  6. filtrationThe solid compound of the title is recovered by filtration

Sources & evidence

ORD record
ord-240c778fe0cb462aa72018d4ba926669
Source dataset
uspto-grants-1990_09
Patent number
US04954508

Reaction notes

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