Carbon Dioxide → 2-Methoxyquinoline-6-carboxylic acid

HRID 986021Notes

Reaction equation

HRID 986021 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[CH:10]2.[C:19](=[O:21])=[O:20]>CCCCCC.C1COCC1>[CH3:18][O:17][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:19]([OH:21])=[O:20])[CH:8]=2)[N:13]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 106575386-Bromo-2-methoxyquinolineHCID 178418339Butyllithium

Product 1

HCID 201589862-Methoxyquinoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyl lithium (63 cm3 of a 1.6M solution in hexane) was added dropwise to a stirred solution of 6-bromo-2-methoxyquinoline (20 g) in THF (250 cm3) at -70° under nitrogen. After 0.5 hours, solid carbon dioxide (50 g) was added, the solution was allowed to warm to room temperature, and volatile material was removed in vacuo. The residue was partitioned between dichloromethane (100 cm3) and water (100 cm3), the aqueous phase was separated and acidified to pH 3.5 with 5M hydrochloric acid. The precipitated solid was filtered and dried (14.2 g). Recrystallisation of a small portion from isopropanol afforded 2-methoxyquinoline-6-carboxylic acid, m.p. 220°-222°.

Workup

  1. customvolatile material was removed in vacuo
  2. customThe residue was partitioned between dichloromethane (100 cm3) and water (100 cm3)
  3. customthe aqueous phase was separated
  4. filtrationThe precipitated solid was filtered
  5. customdried (14.2 g)
  6. customRecrystallisation of a small portion from isopropanol

Sources & evidence

ORD record
ord-53d7a6048c2f4498b9e4a5c5483cfa70
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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