Pentanenitrile, 4,4-dimethyl-3-oxo- → ethyl 2-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)acetate

HRID 631485Notes

Reaction equation

HRID 631485 reaction equation
Cl.[NH:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:3].C([O-])(O)=O.[Na+].[CH3:15][C:16]([CH3:23])([CH3:22])[C:17](=O)[CH2:18][C:19]#[N:20]>CCO>[NH2:20][C:19]1[N:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:3]=[C:17]([C:16]([CH3:23])([CH3:22])[CH3:15])[CH:18]=1

Participants

5

Reactant 3

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 516892Sodium BicarbonateHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 59345794ethyl 2-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-hydrazinylacetate hydrochloride (0.309 g, 2 mmol), NaHCO3 (0.185 g, 2.2 mmol), and 4,4-dimethyl-3-oxopentanenitrile (0.250 g, 2 mmol) in EtOH (10 mL) was heated at 60° C. overnight. The reaction was quenched with water and extracted with CH2Cl2. Extracts were dried over MgSO4 and concentrated under reduced pressure to afford ethyl 2-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)acetate as solid (0.369 g, 82%). 1H NMR (300 MHz, CDCl3) δ 5.50 (s, 1H), 4.75 (s, 2H), 4.23 (q, 2H), 3.57 (br, 2H), 1.29 (t, 3H), 1.25 (s, 9H); LC-MS (ESI) m/z 226 (M+H)+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2
  3. dry with materialExtracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c76cdb9dee844518f985d06a0a149f4
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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