Potassium Hydroxide → HCID 22243516, compound

HRID 890960Notes

Reaction equation

HRID 890960 reaction equation
C[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:13]([OH:15])=[O:14])[N:3]=1.[OH-].[K+]>CCO>[CH3:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[N:3][C:4]([C:13]([OH:15])=[O:14])=[CH:5]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22243345HCID 22243345, compound

Product 1

HCID 22243516HCID 22243516, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 6-methyl-isoquinoline-3-carboxylic acid (0.618 g, 3.07 mmol) is dissolved in 95% EtOH (30 mL). KOH pellets (0.517 g, 9.21 mmol) are added and the reaction is heated at reflux for 1 hour. While heating, a precipitate began to form. Upon cooling, this precipitate (the K+ salt) is filtered and dried at 60° C. in vacuo. The precipitate is dissolved in water and the pH is adjusted to 4–5. The water solution is then loaded onto a column of AGW-×2 resin (H+ form). The resin is rinsed with MeOH, and the desired product is eluted with a solution of 5% TEA in MeOH. The product is concentrated three times from MeOH/MeCN and dried in vacuo. The solid is then dried overnight at 60° C. to yield 6-methyl-isoquinoline-3-carboxylic acid (0.41 g, 71%). HRMS (FAB) calculated for C11H8N O2 K: 188.0711, found 188.0714.

Workup

  1. additionare added
  2. temperaturethe reaction is heated
  3. temperatureat reflux for 1 hour
  4. temperatureWhile heating
  5. customto form
  6. temperatureUpon cooling
  7. filtrationthis precipitate (the K+ salt) is filtered
  8. customdried at 60° C. in vacuo
  9. dissolutionThe precipitate is dissolved in water
  10. washThe resin is rinsed with MeOH
  11. washthe desired product is eluted with a solution of 5% TEA in MeOH
  12. concentrationThe product is concentrated three times from MeOH/MeCN
  13. customdried in vacuo
  14. customThe solid is then dried overnight at 60° C.

Sources & evidence

ORD record
ord-a18d9ad961954a058f037c3c4e361453
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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