Phosphorus oxychloride → 3-chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2-carbonitrile

HRID 240310Notes

Reaction equation

HRID 240310 reaction equation
O[C:2]1[N:7]=[C:6]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:5]2=[N:4][C:3]=1[C:16]#[N:17].O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:2]1[N:7]=[C:6]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:5]2=[N:4][C:3]=1[C:16]#[N:17]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510555HCID 178510555, compound

Product 1

HCID 160653593-chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2-carbonitrileYield 44%

Conditions

Temperature
100 °C

Procedure

A suspension of 6 (671 mg, 3.0 mmol) in POCl3 (8.4 ml) was heated under stirring to 100° C. for 17 h. Excess of POCl3 was evaporated under reduced pressure and the crude was purified by flash chromatography on silica (CH2Cl2), affording 9 (320 mg, 44%) as yellow solid.

Workup

  1. temperaturewas heated
  2. customExcess of POCl3 was evaporated under reduced pressure
  3. customthe crude was purified by flash chromatography on silica (CH2Cl2)

Sources & evidence

ORD record
ord-3ffab4eedf3a45cfb65973262b985db3
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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