Sodium Hydroxide → 1-Chloro-4-trifluoromethylpyridazino[4,5-b]indolizine

HRID 1292063Notes

Reaction equation

HRID 1292063 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[C:15]2[N:14]3[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]3)=[CH:8][C:7]=2[C:6](=O)[NH:5][N:4]=1.P(Cl)(Cl)([Cl:21])=O.[OH-].[Na+]>>[Cl:21][C:6]1[C:7]2[CH:8]=[C:9]3[N:14]([C:15]=2[C:3]([C:2]([F:18])([F:17])[F:1])=[N:4][N:5]=1)[CH:13]=[CH:12][CH:11]=[CH:10]3

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 86752611HCID 86752611, compound

Product 1

HCID 867526121-Chloro-4-trifluoromethylpyridazino[4,5-b]indolizineYield 100%

Procedure

Compound II (2.62 g, 10.3 mmol) and phosphorus oxychloride (3.18 mL, 34 mmoL) were combined and heated under reflux for 2 days. After cooling to room temperature, the reaction mixture was poured into ice water and made basic with aqueous sodium hydroxide (pH>7). The product was collected by filtration and dried in a vacuum oven overnight to give 2.82 g (100%) of 1-chloro-4-trifluoromethylpyridazino[4,5-b]indolizine (III)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 days
  3. filtrationThe product was collected by filtration
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-cbd684199b514920bb4014670a587037
Source dataset
uspto-grants-1998_05
Patent number
US05756501

Reaction notes

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