Acetic Acid → 6-Formyl-4-methoxy-quinoline-3-carboxylic acid

HRID 1297622Notes

Reaction equation

HRID 1297622 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[O:4].[OH-].[Na+].[C:20](O)(=[O:22])C>CO.O>[CH:20]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[C:14]2[O:15][CH3:16])=[O:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 688283896-Iodo-4-methoxy-quinoline-3-carboxylic acid methyl ester

Product 1

HCID 860872056-Formyl-4-methoxy-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To the suspension of 6-iodo-4-methoxy-quinoline-3-carboxylic acid methyl ester (example 1d) (5.91 g, 17.2 mmol) in methanol (20 mL) was slowly added the solution of sodium hydroxide (2.76 g, 69 mmol) in water (10 mL). The mixture was stirred at room temperature for 3 hours. The solution was adjusted pH=5.0 using aqueous acetic acid solution. After adding more water, the solid was collected by filtration, washed with water and dried to obtain 6-formyl-4-methoxy-quinoline-3-carboxylic acid. LC-MS m/e 330 (MH+)

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-da5806025a2e4536baba314cf3d57688
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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