Methanol → Methyl isoquinoline-1-carboxylate

HRID 1476801Notes

Reaction equation

HRID 1476801 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.S(=O)(=O)(O)O.[CH3:19]O>>[C:1]1([C:11]([O:13][CH3:19])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68092Isoquinoline-1-carboxylic acid

Product 1

HCID 21196988Methyl isoquinoline-1-carboxylateYield 100%

Conditions

Temperature
65 °C

Procedure

To a solution of isoquinoline-1-carboxylic acid (10 g, 57.74 mmol) in MeOH (150 mL) was added concentrated sulfuric acid (15 mL) at 0° C. The mixture was warmed to 65° C. and stirred at 65° C. for 24 hours. After cooling to RT, the reaction mixture was partitioned between DCM and saturated aqueous NaHCO3. The organic layer was separated and dried over Na2SO4, and the solvent was evaporated under reduced pressure to give the title compound as a yellow oil (11.2 g, 100%). ESI-MS m/z [M+H]+ 188.

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between DCM and saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2bd7185ff6454d73b20c453da78c13a4
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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