Potassium Hydroxide → 2-Carboxy-7-methyl-4-chloroquinoline

HRID 1827863Notes

Reaction equation

HRID 1827863 reaction equation
[C:1]([C:4]1[CH:13]=[C:12](O)[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[CH:9][CH:10]=2)[N:5]=1)([OH:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:17].[OH-].[Na+].[OH-].[K+]>O=P(Cl)(Cl)Cl>[C:1]([C:4]1[CH:13]=[C:12]([Cl:17])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[CH:9][CH:10]=2)[N:5]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 24819Phosphorus pentachlorideHCID 178418698HCID 178418698, compound

Product 1

HCID 220173932-Carboxy-7-methyl-4-chloroquinolineYield 50%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
130 °C

Procedure

To 20 mL POCl3 was added 2-carboxy-7-methyl-4-hydroxyquinoline (2.5 g, 12.3 mmol) and PCl5 (11.5 g, 55 mmol). The mixture was heated to 130° C. for 3 hours. The reaction mixture was cooled and poured onto ice. The solution was neutralized with solid NaOH and adjusted to pH 11 with solid KOH. The tan precipitate was filtered, slurried in 250 mL water and adjusted to pH 2 with concentrated HCl. The resultant solid was filtered and dried to afford 2-carboxy-7-methyl-4-chloroquinoline (1.34 g, 50%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto ice
  3. filtrationThe tan precipitate was filtered
  4. filtrationThe resultant solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-4d8f06578f8e4844a6d4712a1f10e20d
Source dataset
uspto-grants-2006_06
Patent number
US07056923B2

Reaction notes

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