Methyl 1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylate → HCID 11096910, compound

HRID 1367971Notes

Reaction equation

HRID 1367971 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([O:15][CH3:16])[CH:12]=2)[CH2:7][NH:6]1)=[O:4]>C1(C)C=CC=CC=1.O1CCOCC1.C1COCC1.O=[Mn]=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)=[O:4]

Participants

4

Reactant 1

HCID 5301401Methyl 1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylate

Product 1

HCID 11096910HCID 11096910, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 70182102HCID 70182102, compoundSolvent

Procedure

1.8 g (6.26 mmol) of 6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester and 3.3 g (37.6 mmol) of MnO2 in toluene/dioxane/THF was heated under reflux overnight. After gravity filtration, the hot filtrate was evaporated to produce 0.4 g (1.62 mmol, 26%) of 6,7-dimethoxy-isoquinoline-3-carboxylic acid methyl ester. LCMS: 248 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. filtrationAfter gravity filtration
  3. customthe hot filtrate was evaporated

Sources & evidence

ORD record
ord-7bdf2be94a2b4e1197c0b5f61e53e711
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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