Water → HCID 86729280, compound

HRID 1051504Notes

Reaction equation

HRID 1051504 reaction equation
Cl[C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][NH:12][NH2:13].O>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:3]2[C:2](=[N:13][N:12]([CH3:11])[CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 122593832,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 86729280HCID 86729280, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2,6-dichloronicotinaldehyde (600 mg, 3.41 mmol) in THF (5 mL) was added CH3NHNH2 (480 mg, 4.1 mmol) in a seal tube at 26° C. The mixture was stirred for 16 h at 120° C. until the reaction was complete. The mixture was then treated with water (20 ml) and extracted with ethyl acetate (3×20 ml) and the combined organic layers washed with brine (20 ml), dried over Na2SO4 and concentrated to get the crude material, which was purified by column chromatography to yield the desired compound as a yellow solid (380 mg, 72.4%) (420 mg, Yield 75%).

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washthe combined organic layers washed with brine (20 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto get the crude material, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-645c49e959d54e1395c147d97e0f9975
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

Loading…