Dimethylformamide → 5-chloro-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 1096993Notes

Reaction equation

HRID 1096993 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[CH3:11][C:12]1[CH:16]=[C:15](O)[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:13]=1>>[Cl:3][C:15]1[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:13]=[C:12]([CH3:11])[C:16]=1[CH:9]=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178429262HCID 178429262, compound

Product 1

HCID 121019265-chloro-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Conditions

Temperature
80 °C

Procedure

In a 1.0-liter egg plant-type flask, POCl3 (56 mL, 0.60 mL) was dropwise added to a DMF (17.4 mL, 0.23 mol) solution of 3-methyl-1-pyridin-2-yl-1H-pyrazol-5-ol with cooling with ice, and stirred overnight at 80° C. The reaction solution was poured onto crushed ice, and stirred at room temperature. The formed precipitate was filtered, and dried under reduced pressure to obtain the title compound as a pale brown solid.

Workup

  1. temperaturewith cooling with ice
  2. additionThe reaction solution was poured
  3. customonto crushed ice
  4. stirringstirred at room temperature
  5. filtrationThe formed precipitate was filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e2a6b5d6329349f88d6f67a969ef8ace
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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