Methyl iodide → HCID 68530781, compound

HRID 2374168Notes

Reaction equation

HRID 2374168 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:16](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O>[CH3:16][O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12554535Methyl 3-hydroxyquinoline-4-carboxylate

Product 1

HCID 68530781HCID 68530781, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Methyl 3-hydroxycinchoninate, (J. Org. Chem. 1953, 18, 552) (1.53 g, 7.54 mmol), potassium carbonate (1.15 g, 8.29 mmol) in acetone (11 ml) was treated with methyl iodide (470 uL, 7.54 mmol) was stirred at RT under nitrogen overnight. The mixture diluted with water and extracted into DCM and washed with satd. sodium thiosulfate solution. The organics were dried over Na2SO4 and concentrated. Material purified by SGC (Combi flash, 10-50% EtOAc-hexanes over 40 minutes) gave methyl 3-methoxycinchoninate. 1H NMR (CDCl3) δ 8.85 (s, 1H), 8.07 (d, 1H), 7.72 (d, 1H), 7.61 (m, 2H), 4.08 (s, 3H), 4.03 (s, 1H). MS (ESI+) for m/z 218 (M+H)+.

Workup

  1. extractionextracted into DCM
  2. washwashed with satd
  3. dry with materialThe organics were dried over Na2SO4
  4. concentrationconcentrated
  5. customMaterial purified by SGC (Combi flash, 10-50% EtOAc-hexanes over 40 minutes)

Sources & evidence

ORD record
ord-498537dc2b944f23a1d1ab66dd0b15b4
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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