Hydrazine → HCID 178434583, compound

HRID 1466593Notes

Reaction equation

HRID 1466593 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9](=[N:13]O)[C:10](=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.[NH2:16][NH2:17]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:17][N:16]=[C:10]([CH3:11])[C:9]=2[NH2:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178468377HCID 178468377, compound

Product 1

HCID 178434583HCID 178434583, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. solution of 1-(3-chlorophenyl)-2-(hydroxyimino)butane-1,3-dione (224.8 mg, 0.996 mmol) in 5 mL ethanol was dropwise added hydrazine (0.30 mL, 9.6 mmol). The reaction was warmed to room temperature and stirred for 15 hours. The crude reaction mixture was concentrated and purified by flash chromatography on silica gel (20 to 100% ethyl acetate in dichloromethane) to yield 113.3 mg (55%) of 5-(3-chlorophenyl)-3-methyl-1H-pyrazol-4-amine. LCMS (ESI) m+H=208.2; 1H NMR (400 MHz, DMSO-d6) δ: 12.20 (s, 1H), 7.94-7.57 (m, 2H), 7.40 (s, 1H), 7.27 (d, J=9.1, 1H), 2.12 (s, 3H).

Workup

  1. customTo a 0° C.
  2. customThe crude reaction mixture
  3. concentrationwas concentrated
  4. custompurified by flash chromatography on silica gel (20 to 100% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-070f98c8e23c446590617b9707ae33ca
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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