Phosphorus oxychloride → HCID 57654529, compound

HRID 1661815Notes

Reaction equation

HRID 1661815 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11](O)[CH2:10][CH:9]=[CH:8]2.P(Cl)(Cl)([Cl:19])=O>>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([Cl:19])[CH:9]=[CH:8]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67429372HCID 67429372, compound

Product 1

HCID 57654529HCID 57654529, compoundYield 20%

Procedure

(1-Hydroxy-quinolin-6-yl)-acetic acid methyl ester (1.0 g, 4.61 mmol) was refluxed for 25 minutes in phosphorous oxychloride (30 mL). The excess phosphorous oxychloride was evaporated, saturated sodium bicarbonate was added and the crude mixture was extracted several times with ethyl acetate. The product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 0.219 g (20%) of (2-chloro-quinolin-6-yl)-acetic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 7.99 (d, 1H, J=8.4 Hz), 7.93 (d, 1H, J=8.8 Hz), 7.63 (m, 1H), 7.60 (dd, 1H, J=2.0, 8.4 Hz), 7.30 (d, 1H, J=8.8 Hz), 3.73 (s, 2H), 3.64 (s, 3H).

Workup

  1. customThe excess phosphorous oxychloride was evaporated
  2. additionsaturated sodium bicarbonate was added
  3. extractionthe crude mixture was extracted several times with ethyl acetate
  4. customThe product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c8055693335d4b25accd4c09b97e3d9b
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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