Methanol → HCID 59756874, compound

HRID 2196590Notes

Reaction equation

HRID 2196590 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][OH:46].CN(C)[CH:49]=[O:50]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[C:45]([O:50][CH3:49])=[O:46]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 59756874HCID 59756874, compound

Reagents, catalysts & solvents 2

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalyst2×

Conditions

Temperature
85 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (3 g, 13.45 mmol), palladium acetate (605 mg, 2.69 mmol) and 1,3-bis(diphenylphosphino)propane (1.39 g, 3.36 mmol) were added to a pressure tube then dissolved in N,N-dimethylformamide (25 mL). Carbon monoxide gas was bubbled through the mixture for 10-15 minutes. The reaction mixture was heated at 85° C. overnight. Additional palladium acetate (303 mg, 1.35 mmol), 1,3-bis(diphenylphosphino)propane (277 mg, 0.671 mmol) and methanol (2 mL) were added to the reaction mixture then carbon monoxide was bubbled through the solution for 10 minutes. The reaction mixture was then heated at 85° C. overnight again. The mixture was concentrated under vacuum. The crude material was purified twice by silica gel chromatography (1% methanol/dichloromethane then 50%-67% ethyl acetate/hexane) to afford methyl 6,7-dimethoxyquinoline-4-carboxylate (2.07 g) as a light yellow solid. MS (ESI, pos. ion) m/z: 248.0 (M+1).

Workup

  1. customCarbon monoxide gas was bubbled through the mixture for 10-15 minutes
  2. customcarbon monoxide was bubbled through the solution for 10 minutes
  3. temperatureThe reaction mixture was then heated at 85° C. overnight again
  4. concentrationThe mixture was concentrated under vacuum
  5. customThe crude material was purified twice by silica gel chromatography (1% methanol/dichloromethane

Sources & evidence

ORD record
ord-31bbea308d3b4dc2b7941fa7963a5751
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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