Methanol → HCID 54442354, compound

HRID 1974659Notes

Reaction equation

HRID 1974659 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:15]([O:17]C)=[O:16])=[C:8]([C:11]([O:13]C)=O)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+].S(=O)(=O)(O)O>CC(C)=O.C(OC(=O)C)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[C:15](=[O:16])[O:17][C:11](=[O:13])[C:8]=3[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19101938Dimethyl 6,7-quinolinedicarboxylate

Product 1

HCID 54442354HCID 54442354, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of dimethyl 6,7-quinolinedicarboxylate (3.00 g, 12.2 mmol), methanol and 10% aqueous sodium hydroxide (25 mL, 62.5 mmol) is stirred overnight at room temperature, cooled, acidified to pH 4-5 with concentrated sulfuric acid, diluted with acetone and filtered. The filtrate is concentrated in vacuo to give a tan solid, which is suspended in acetic anhydride (100 mL), stirred overnight at 56° C. and cooled. The solvent is removed in vacuo to afford the title product as a tan solid (1.20 g, 49.4%) identified by 1HNMR and IR spectral analyses.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give a tan solid, which
  5. stirringstirred overnight at 56° C.
  6. temperaturecooled
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9795ddaf55374f809c49e75ab1b5533e
Source dataset
uspto-grants-1994_02
Patent number
US05283335

Reaction notes

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