Acetic Acid → Methyl Quinoline-8-Carboxylate

HRID 472789Notes

Reaction equation

HRID 472789 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:18]([OH:20])=[O:19])[CH:11]=[CH:10][CH:9]=1.C(O)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:18]([O:20][CH3:1])=[O:19])[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 665828-Quinolinecarboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 12554533Methyl Quinoline-8-CarboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of (trimethylsilyl)diazomethane (8.0 mL of a 2.0 M solution in hexanes, 16.0 mmol) was added slowly to a suspension of quinoline-8-carboxylic acid (2.0 g, 11.5 mmol) in toluene (80 mL) and MeOH (12 mL) at 0° C. After 30 min at 0° C., the reaction mixture was warmed to room temperature and stirred for 64 h. Aqueous acetic acid was added and then enough saturated aqueous Na2CO3 was added to bring the pH to 7.5. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phase was dried (MgSO4SO4), filtered and concentrated in vacuo. The resulting brown oil was purified on 40 g silica gel (2:1 CH2Cl2/EtOAc) to afford 1.72 g (80%) of methyl quinoline-8-carboxylate.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic phase was dried (MgSO4SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting brown oil was purified on 40 g silica gel (2:1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-e46c9b6757464243a3b4e34f1729b547
Source dataset
uspto-grants-2014_01
Patent number
US08633220B2

Reaction notes

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