Ethanol → 2-(5-amino-1-p-tolyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol

HRID 220215Notes

Reaction equation

HRID 220215 reaction equation
[OH:1][CH2:2][C:3]([CH3:10])([CH3:9])[C:4](=O)[CH2:5][C:6]#[N:7].Cl[NH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20](O)C>>[NH2:7][C:6]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[N:12]=[C:4]([C:3]([CH3:10])([CH3:9])[CH2:2][OH:1])[CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 120447945-Hydroxy-4,4-dimethyl-3-oxopentanenitrileHCID 205084581-Chloro-2-phenylhydrazine

Product 1

HCID 111183102-(5-amino-1-p-tolyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol

Conditions

Temperature
90 °C

Procedure

5-hydroxy-4,4-dimethyl-3-oxopentanenitrile (0.32 g, 2.27 mmol) and 1-chloro-2-phenylhydrazine (0.361 g, 2.49 mmol) were combined in ethanol and heated at 90° C. for 8 hours. The reaction was cooled and concentrated, and the residue was triturated with ethyl acetate. The solids were collected by filtration, triturated with acetone and rinsed to isolate 36 mg of the title compound as a pure white solid. MS M+1(246).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customthe residue was triturated with ethyl acetate
  4. filtrationThe solids were collected by filtration
  5. customtriturated with acetone
  6. washrinsed

Sources & evidence

ORD record
ord-728472c4e07a41d58017348cafe6c70c
Source dataset
uspto-grants-2012_06
Patent number
US08202899B2

Reaction notes

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