Pyridine → HCID 45480238, compound

HRID 1432864Notes

Reaction equation

HRID 1432864 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[N:8][NH:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.O=P(Cl)(Cl)[Cl:21]>ClC1C=CC=CC=1>[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[N:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 20164596HCID 20164596, compound

Product 1

HCID 45480238HCID 45480238, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

7-Methyl-1-H-cinnolin-4-one (1.3 g, 8.1 mmol) is treated with about 80 mL of chlorobenzene and heated until the solid dissolves. The resulting solution is cooled and treated with pyridine (0.16 mL, 2 mmol) and POCl3 (1.13 mL, 12.2 mmol). The solution is heated to reflux for 1 h then concentrated to dryness. The residue is chromatographed (20% ethyl acetate/hexane) to yield the title compound as a tan solid (˜1 g, 5.6 mmol). MS m/z (M+=178); 1H NMR (CDCl3, 300 MHz) δ9.3 (s, 1H), 8.35 (s, 1H), 8.1 (d, 1H), 7.7 (d, 1H), 2.68 (s, 3H).

Workup

  1. temperatureheated until the solid
  2. dissolutiondissolves
  3. temperatureThe resulting solution is cooled
  4. temperatureThe solution is heated
  5. temperatureto reflux for 1 h
  6. concentrationthen concentrated to dryness
  7. customThe residue is chromatographed (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b062788de6384089afae877869bcc373
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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