Acetic Acid → 6-Isoquinolinecarboxylic acid, methyl ester

HRID 2289495Notes

Reaction equation

HRID 2289495 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[C:13](O)(=[O:15])C>[C-]#N.[Na+].O=[Mn]=O>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:15][CH3:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 15290359Isoquinoline-6-carboxaldehyde

Product 1

HCID 152903606-Isoquinolinecarboxylic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8929Sodium CyanideSolvent

Procedure

290 mg of isoquinoline-6-carbaldehyde are dissolved in 40 ml of MeON, and firstly 450 mg of NaCN, then 210 μl of glacial acetic acid, and finally 3.5 g of MnO2 are added. The mixture is stirred at RT for 3 days, and the precipitate is filtered off and the filtrate is poured into a solution of 15 g of FeSO4 in 150 ml of water. Subsequently, the pH of the mixture is adjusted to 9 with Na2CO3 solution, the precipitate is filtered off, and the filtrate is extracted 3× with 150 ml of EA. Drying takes place over Na2SO4, and the solvent is removed in vacuo. 190 mg are obtained of a colorless oil, which in reacted without any further purification.

Workup

  1. filtrationthe precipitate is filtered off
  2. additionthe filtrate is poured into a solution of 15 g of FeSO4 in 150 ml of water
  3. filtrationthe precipitate is filtered off
  4. extractionthe filtrate is extracted 3× with 150 ml of EA
  5. customDrying
  6. customthe solvent is removed in vacuo
  7. custom190 mg are obtained of a colorless oil, which
  8. customin reacted without any further purification

Sources & evidence

ORD record
ord-412978cf007f4a3da45f23db6bad96f1
Source dataset
uspto-grants-2000_07
Patent number
US06093729

Reaction notes

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