Water → 8-methyl-2-pyridin-2-ylquinoline-4-carboxylic acid

HRID 1199939Notes

Reaction equation

HRID 1199939 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[CH3:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17](=[O:20])[C:16]2=O.[OH2:22].[OH-].[K+]>CCO>[CH3:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH:2]=[C:16]2[C:17]([OH:20])=[O:22]

Participants

6

Reactant 4

HCID 962Water2×HCID 142862-AcetylpyridineHCID 143137-MethylisatinHCID 14797Potassium Hydroxide

Product 1

HCID 38045488-methyl-2-pyridin-2-ylquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 2-acetylpyridine (IV; R1 =2-aza: 6.05 g, 0.05 mol) and 7-methylisatin (V; R2 =H: 8.52 g, 0.053 mol) in 65 mL of 50% EtOH--H2O containing KOH (13 g) was refluxed for 2 h, then diluted with 50% EtOH--H2O to obtain a homogeneous solution, filtered and acidified (HOAc). The resulting acid was collected, washed with 30% EtOH--H2O and recrystallized from DMF--EtOH to provide the product (9.4 g, 67%, mp. 319°-320° C. Anal. (C16H12N2O2) C,H,N.

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationfiltered
  3. customThe resulting acid was collected
  4. washwashed with 30% EtOH
  5. customH2O and recrystallized from DMF
  6. customEtOH to provide the product (9.4 g, 67%, mp. 319°-320° C

Sources & evidence

ORD record
ord-1162362d0d804a81b55043c782955c42
Source dataset
uspto-grants-1990_02
Patent number
US04904659

Reaction notes

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