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

HRID 6684Notes

Reaction equation

HRID 6684 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-bcd19a03fab24805954e9d09cca356c1
Source dataset
uspto-grants-2006_08
Patent number
US07084142B2

Reaction notes

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