Phosphorus oxychloride → HCID 10539447, compound

HRID 1934965Notes

Reaction equation

HRID 1934965 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][CH:9]=[C:8]([C:16]#[N:17])[C:7]2=O)[CH3:2].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:7]1[C:6]2[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[N:10]=[CH:9][C:8]=1[C:16]#[N:17]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10490471HCID 10490471, compound

Product 1

HCID 10539447HCID 10539447, compound

Procedure

A mixture of 7.95 g (32.6 mmol) of 6-ethoxy-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile and 50 mL of phosphorous oxychloride was refluxed for 3 h 40 min. The phosphorous oxychloride was removed in vacuo and the residue was slurried with ice water. Solid NaHCO3 was added (pH8) and the product was collected by filtration, washed well with water and dried in vacuo (40° C.). The yield was 7.75 g of 4-chloro-6-ethoxy-7-methoxyquinoline-3-carbonitrile as a tan solid: mass spectrum (electrospray, m/e): M+H 262.8, 264.8.

Workup

  1. temperaturewas refluxed for 3 h 40 min
  2. customThe phosphorous oxychloride was removed in vacuo
  3. additionSolid NaHCO3 was added (pH8)
  4. filtrationthe product was collected by filtration
  5. washwashed well with water
  6. customdried in vacuo (40° C.)

Sources & evidence

ORD record
ord-d53706d079604bf6b6be87b5ad41e747
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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