Ammonia → HCID 18676113, compound

HRID 1635505Notes

Reaction equation

HRID 1635505 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.N.[CH3:22][N:23](C=O)[CH3:24]>>[CH3:22][N:23]([CH3:24])[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 114829832-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Product 1

HCID 18676113HCID 18676113, compoundYield 78%

Conditions

Temperature
180 °C

Procedure

A mixture of 2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 45; 0.91 g, 0.0032 mol) and 50 mL of liquid ammonia in 20 mL of DMF was stirred in a sealed tube under 1800 psi, at 180° C. for 72 hours. After the solution was cooled, the solvent was removed under vacuum and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8) to give 0.73 g (78% yield) of product as a yellow crystal: mp: 84-85° C.; Anal. Calc'd. for C18H20N4: C, 73.94; H, 6.89; N. 19.16. Found: C, 73.68; H, 6.74; N, 19.13.

Workup

  1. temperatureAfter the solution was cooled
  2. customthe solvent was removed under vacuum
  3. customthe residue was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8)

Sources & evidence

ORD record
ord-c69ef2cc22b942fb8bccbd6db20eaca5
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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