Tetrahydrofuran → 8-Methoxy-2-methylquinoline-5-carboxylic acid

HRID 2393086Notes

Reaction equation

HRID 2393086 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:42].[O:43]1[CH2:47]CCC1>O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:13][O:12][C:9]1[C:8]2[N:7]=[C:6]([CH3:14])[CH:5]=[CH:4][C:3]=2[C:2]([C:47]([OH:43])=[O:42])=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 47150215-Bromo-8-methoxy-2-methylquinolineHCID 178418416HCID 178418416, compound

Product 1

HCID 189790708-Methoxy-2-methylquinoline-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixtures of 5-bromo-8-methoxy-2-methylquinoline (2.0 g), triethylamine (11 ml), triphenylphosphine (0.79 g), and bis(tripbenylphosphine)palladium (II) chloride (1.56 g) in tetrahydrofuran (200 ml) and water (90 ml) was stirred in a pressurised reaction vessel and charged with carbon monoxide to a pressure of 160 psi. The vessel was heated to 80° C. and stirred for 72 hours. The reaction was allowed to cool and depressurised. The mixture was filtered ant the organic solvent was removed in vacuo. The aqueous residue was basified with 1M sodium hydroxide and washed with ethyl acetate (300ml). The aqueous solution was acidified to pH 5 with glacial acetic acid and extracted with ethyl acetate (2×400 ml). The organic extracts were combined, dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo to yield the title product (1.0 g) as an off-white solid.

Workup

  1. temperatureto cool
  2. filtrationThe mixture was filtered ant the organic solvent
  3. customwas removed in vacuo
  4. washwashed with ethyl acetate (300ml)
  5. extractionextracted with ethyl acetate (2×400 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-2f6f410569284a44a78b8eda99f401bd
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

Loading…