Phosphorus oxychloride → 3-Chloro-6-(2,4-dimethylphenyl)pyridazine

HRID 1625569Notes

Reaction equation

HRID 1625569 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12](=O)[NH:13][N:14]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:12]1[N:13]=[N:14][C:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 4418957HCID 4418957, compound

Product 1

HCID 123687643-Chloro-6-(2,4-dimethylphenyl)pyridazine

Procedure

6-(2,4-dimethylphenyl)pyridazin-3(2H)-one (example 13c) was heated with POCl3 (5.15 ml, 55 mmol) at 85° C. for 4 hours. Following cooling and treating with crushed ice a white solid obtained and was collected to give 1.36 g of the 3-chloro-6-(2,4-dimethylphenyl)pyridazine. 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.34 (s, 3H), 7.16-7.19 (m, 2H), 7.35-7.37 (d, 1H), 7.93-8.00 (dd, 2H); (M+H, 313).

Workup

  1. temperatureFollowing cooling
  2. additiontreating with crushed ice a white solid
  3. customobtained
  4. customwas collected

Sources & evidence

ORD record
ord-e579fcd79eea4cfca6b00213b0275c93
Source dataset
uspto-grants-2014_07
Patent number
US08784782B2

Reaction notes

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