Phosphorus oxychloride → Methyl 4,7-dichloroquinoline-2-carboxylate

HRID 1353438Notes

Reaction equation

HRID 1353438 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13](O)[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].O=P(Cl)(Cl)[Cl:19]>>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([Cl:19])[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178498504HCID 178498504, compound

Product 1

HCID 29923275Methyl 4,7-dichloroquinoline-2-carboxylateYield 95.2%

Conditions

Temperature
140 °C

Procedure

7-Chloro-4-hydroxy-2-quinolinecarboxylic acid methyl ester (76 g) was added to POCl3 (100 mL) at rt, and heated at 140 degrees C. for 1 h, then cooled to rt. After the removal of excess POCl3 in vacuo, cold 1 N NaOH solution was added to pH 8, and precipitated solid was triturated, washed with water and dried under vacuum to afford 78 g (95.2%) of 4,7-dichloro-2-quinolinecarboxylic acid methyl ester as an off-white powder. LC-MS, 255 (M++1). 1H NMR (DMSO-d6): δ 3.95 (s, 3H), 7.91 (d, 1H), 8.22 (s, 1H), 8.26 (d, 1H), 8.33 (s, 1H).

Workup

  1. temperaturecooled to rt
  2. customAfter the removal of excess POCl3 in vacuo, cold 1 N NaOH solution
  3. additionwas added to pH 8
  4. customprecipitated solid
  5. customwas triturated
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6037a7cf93ec43809aa002597eed6c51
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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