Methylhydrazine → HCID 68161400, compound

HRID 2368673Notes

Reaction equation

HRID 2368673 reaction equation
F[C:2]1[C:3]([C:11](=O)[CH3:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9].[CH3:14][NH:15][NH2:16]>>[CH:8]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]2[C:11]([CH3:12])=[N:16][N:15]([CH3:14])[C:2]=12)([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 67083167HCID 67083167, compound

Product 1

HCID 68161400HCID 68161400, compound

Conditions

Temperature
140 °C

Procedure

1-(3-Fluoro-4-isopropyl-pyridin-2-yl)-ethanone (prepared in the previous step, 2.50 g, 15.15 mmol) and methyl hydrazine (1.04 g, 23.00 mmol) were combined in 8 mL of glycol. The reaction solution was stirred at 140° C. for 2 hours. After cooling, it was quenched with water, extracted with DCM, then washed with water, brine and concentrated. Column chromatography using 15 to 35% ethyl acetate in hexane as eluant afforded the title compound as a pale yellow solid. Spectroscopic data: 1H-NMR (300 MHz, CDCl3): δ ppm 1.39 (d, J=6.73 Hz, 6 H), 2.64 (s, 3 H), 3.65 (hept, J=6.73 Hz, 1 H), 4.23 (s, 3 H), 7.14 (d, J=4.69 Hz, 1 H), 8.44 (d, J=4.69 Hz 1 H).

Workup

  1. temperatureAfter cooling
  2. customit was quenched with water
  3. extractionextracted with DCM
  4. washwashed with water, brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f8f4fa98d29f41cead10530d90d006b3
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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