Phosphorus oxychloride → HCID 86606406, compound

HRID 2375424Notes

Reaction equation

HRID 2375424 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=O)[NH:19][N:20]=[C:21]3[CH3:25])=[C:16]2[CH3:27])=[CH:11][CH:10]=1)[CH3:7]>>[Cl:3][C:18]1[C:17]2=[C:16]([CH3:27])[N:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:6][CH3:7])=[CH:10][CH:11]=3)[C:23]([CH3:24])=[C:22]2[C:21]([CH3:25])=[N:20][N:19]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69275510HCID 69275510, compound

Product 1

HCID 86606406HCID 86606406, compound

Procedure

A solution of POCl3 (15 mL) and 6-(4-ethoxyphenyl)4,5,7-trimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one (1.5 g) were combined and heated at reflux for 48 h. The reaction mixture was allowed to cool to rt, and was quenched by the careful addition of water (50 mL) followed by a saturated aqueous solution NaHCO3 (50 mL). The reaction mixture was extracted with CH2Cl2 (5×50 mL), and the combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield 1-chloro-6-(4-ethoxyphenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine as a yellow/green solid. MS (ESI) 316 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. customwas quenched by the careful addition of water (50 mL)
  4. extractionThe reaction mixture was extracted with CH2Cl2 (5×50 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65ec125367064bc0ae44e177cdd834d3
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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