Methanol → Methyl isoquinoline-5-carboxylate

HRID 1051239Notes

Reaction equation

HRID 1051239 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.S(=O)(=O)(O)O.[CH3:19]O>>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:19])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 260936Isoquinoline-5-carboxylic acid

Product 1

HCID 313259Methyl isoquinoline-5-carboxylateYield 96%

Procedure

Isoquinoline-5-carboxylic acid (5.6 g, 32.36 mmol) obtained in Step (2) above and methanol (90 mL) were mixed and stirred. The reaction solution was slowly added with sulfuric acid (15 mL, 259 mmol) and refluxed for about 20 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled under reduced pressure. The concentrate was added with distilled water and adjusted to have a pH value in a range of 10˜11 by adding DIPEA. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (5.8 g, 96%).

Workup

  1. temperaturerefluxed for about 20 hours
  2. distillationthe solvent was distilled under reduced pressure
  3. additionThe concentrate was added with distilled water
  4. additionby adding DIPEA
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  7. customThe organic layer thus obtained
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfd15df771f94972a65eaf361220b754
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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