Phosphorus oxychloride → HCID 22458564, compound

HRID 2185460Notes

Reaction equation

HRID 2185460 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[CH2:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]2[Cl:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11529633HCID 11529633, compound

Product 1

HCID 22458564HCID 22458564, compound

Procedure

A mixture of ethyl 6-benzyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (A, 1.96 g) and phosphorus oxychloride (10 mL) was refluxed for 15 min. The solution was poured into ice water containing concentrated ammonia solution (15 mL), and the resulting mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to afford crude the title compound (2.77 g) as a brown oil: 1H NMR (400 MHz, CDCl3) δ 1.48 (t, J=6.8 Hz, 3H), 4.31 (s, 2H), 4.55 (q, J=6.8 Hz, 2H), 7.18-7.41 (m, 5H), 7.99 (d, J=8.8 Hz, 1H), 8.39 (s, 1H), 8.61 (d, J=8.8 Hz, 1H), and 9.38 (s, 1H).

Workup

  1. temperaturewas refluxed for 15 min
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1d000f7050d8400ca4458a1838305a4e
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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