Phosphorus oxychloride → HCID 67083777, compound

HRID 2239513Notes

Reaction equation

HRID 2239513 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][N:8]=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]2=O.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[N:8][C:7]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67083717HCID 67083717, compound

Product 1

HCID 67083777HCID 67083777, compoundYield 88%

Procedure

To a 50 mL round bottom flask charged with a magnetic stir bar and ethyl 6,7-dimethoxy-4-oxo-1,4-dihydrocinnoline-3-carboxylate (1.00 g, 3.6 mmol) (Method 5) was added phosphorous oxychloride (15 mL). The reaction flask was fitted with a reflux condenser and heated to reflux for 2 h before being allowed to cool to rt. The crude reaction mixture was concentrated in vacuo, and the residue was treated with aqueous NaHCO3 (˜25 mL). The crude product precipitated from solution and was collected via vacuum filtration using a Buchner funnel. The solid was washed water (1×100 mL) and diethyl ether (1×100 mL) to yield 0.941 g (88%) of the title compound as a light brown solid that was used without further purification. 1H NMR: 7.98 (s, 1H), 7.50 (s, 1H), 4.55 (q, 2H), 4.13 (s, 6H), 1.45 (t, 3H); m/z 298.

Workup

  1. additionTo a 50 mL round bottom flask charged with a magnetic stir bar
  2. customThe reaction flask was fitted with a reflux condenser
  3. temperatureheated
  4. temperatureto reflux for 2 h
  5. customThe crude reaction mixture
  6. concentrationwas concentrated in vacuo
  7. additionthe residue was treated with aqueous NaHCO3 (˜25 mL)
  8. customThe crude product precipitated from solution
  9. filtrationwas collected via vacuum filtration
  10. washThe solid was washed water (1×100 mL) and diethyl ether (1×100 mL)

Sources & evidence

ORD record
ord-6cdd2b0a7ca5472ba43977607615bf72
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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