Methanol → Methyl 1-butylisoquinoline-7-carboxylate

HRID 14268Notes

Reaction equation

HRID 14268 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[CH3:23]O>>[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:23])=[O:16])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 210851771-Butylisoquinoline-7-carboxylic acid

Product 1

HCID 21086138Methyl 1-butylisoquinoline-7-carboxylate

Procedure

A solution of 1-butylisoquinoline-7-carboxylic acid (325 mg, 1.41 mmol) in methanol (25 mL) containing concentrated sulfuric acid (800 μL) was refluxed overnight. The reaction mixture was then concentrated under reduced pressure, diluted with methylene chloride, washed with water, and saturated sodium chloride. The organic layer was then dried (sodium sulfate), filtered, and concentrated to yield methyl 1-butylisoquinoline-7-carboxylate (350 mg): ESI MS m/z 244 [M+H]+;

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. additiondiluted with methylene chloride
  4. washwashed with water, and saturated sodium chloride
  5. dry with materialThe organic layer was then dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7a3169cd7e464668803ed69980273ac8
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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