Methanol → Methyl (1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

HRID 1642114Notes

Reaction equation

HRID 1642114 reaction equation
[CH:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.OS(O)(=O)=O.[CH3:20]O>>[CH3:20][O:13][C:12](=[O:14])[CH2:11][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2733683(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid

Product 1

HCID 45588337Methyl (1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

Procedure

2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid (7.90 g, 41.3 mmol) was dissolved in methanol (200 ml), and H2SO4 (4.4 ml, 82.6 mmol) was added under a nitrogen atmosphere. The reaction solution was heated under reflux and, when the reaction was complete, was stirred overnight at room temperature. The methanol was removed in vacuo and the resulting residue was taken up in ethyl acetate (200 ml). The solution was washed with saturated NaHCO3 solution (150 ml), dried (sodium sulfate) and concentrated.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux
  3. customThe methanol was removed in vacuo
  4. washThe solution was washed with saturated NaHCO3 solution (150 ml)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e88a7c0b34b54bc0b2db5d304f50bcec
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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