Phosphorus oxychloride → HCID 57654529, compound

HRID 1921639Notes

Reaction equation

HRID 1921639 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-f4bea69c0a704ac1888c0d79ff15db2c
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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