Phosphorus oxychloride → HCID 66637025, compound

HRID 1094666Notes

Reaction equation

HRID 1094666 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][NH:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:23]>>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:23])=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12807908HCID 12807908, compound

Product 1

HCID 66637025HCID 66637025, compound

Conditions

Temperature
120 °C

Procedure

A mixture of Ethyl 7-tert-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (4.54 g, 16.6 mmol) in POCl3 (60 ml) was heated at 120° C. for 3 hours. After the solvent was evaporated in vacuo, the residue was diluted with CH2Cl2. The organic layer was poured into ammonia-water with ice-cooling. The aqueous layer was extracted with CH2Cl2 and the organic layer was washed with water, dried over sodium sulfate and concentrated in vacuo to give crude product. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (8:1 to 6:1) to give the title compound (4.82 g) as colorless oil. 1H NMR (270 MHz, DMSO-d6) δ ppm 1.35-1.44 (3H, m), 1.42 (9H, s), 4.38-4.49 (2H, m), 7.97-8.06 (2H, m), 8.30-8.36 (1H, m),9.15 (1H, s).

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. additionthe residue was diluted with CH2Cl2
  3. additionThe organic layer was poured into ammonia-water with ice-
  4. temperaturecooling
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. washthe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give crude product
  10. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (8:1 to 6:1)

Sources & evidence

ORD record
ord-3709037c3de94a03a7baea13a0c36840
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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