Methylhydrazine → 3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amine

HRID 474343Notes

Reaction equation

HRID 474343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=O)[C:10]([N:15]1C(=O)C2C(=CC=CC=2)C1=O)=[CH:11][N:12](C)[CH3:13].C[NH:28]N>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[C:10]([NH2:15])=[CH:11][N:12]([CH3:13])[N:28]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 666776892-(3-(2,5-Dichlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione

Product 1

HCID 580630233-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amineYield 38.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled solution of 2-(3-(2,5-Dichlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione (0.050 g, 0.13 mmol) in ethanol (6 mL) was added 40% aqueous methylhydrazine solution (45 mg, 0.39 mmol). The mixture was then heated at reflux for 3 hours. The reaction mixture was then concentrated and purified by flash column chromatography to afford 3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amine as a solid (12 mg, 38% yield). 1H NMR (400 MHz, CDCl3): 7.50 (d, J=3.6 Hz, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.28 (m, 1H), 7.06 (s, 1H), 3.86 (s, 3H), 2.98 (s, 2H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was then concentrated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-b168f3f2bbc848b9ba45127cfef64a8d
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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