6,7-Dimethoxy-4-isoquinolineacetic acid → HCID 88490592, compound

HRID 1165870Notes

Reaction equation

HRID 1165870 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][CH:7]=[C:6]2[CH2:15][C:16]([OH:18])=[O:17].[CH3:19][NH:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[CH:30]=2)[C:25]1=[O:38]>CN(C)C=O>[OH2:2].[CH3:19][N:20]([C:16](=[O:18])[CH2:15][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=[N:8][CH:7]=1)[CH2:21][CH2:22][CH2:23][N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[CH:30]=2)[C:25]1=[O:38].[CH3:19][N:20]([CH2:21][CH2:22][CH2:23][N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[CH:30]=2)[C:25]1=[O:38])[C:16](=[O:17])[CH2:15][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 123788106,7-Dimethoxy-4-isoquinolineacetic acidHCID 14154484HCID 14154484, compound

Product 1

HCID 88490592HCID 88490592, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.2 g (20 mmol) of N,N'-carbonyl-diimidazole are added to a solution of 4.9 g (17 mmol) of 6,7-dimethoxy-isoquinolin-4-yl-acetic acid in 100 ml of dimethylformamide. After about 30 minutes 4.8 g (17 mmol) of 2-(3-methylamino-propyl)-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are added and the mixture is stirred for 2 hours at ambient temperature. The solvent is evaporated off in vacuo and the residue remaining is dissolved in a mixture of 2 molar sodium hydroxide solution and methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated down in vacuo.

Workup

  1. customThe solvent is evaporated off in vacuo
  2. dissolutionthe residue remaining is dissolved in a mixture of 2 molar sodium hydroxide solution and methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down in vacuo

Sources & evidence

ORD record
ord-0355a1660f1343b69f3a7bb57f43cda6
Source dataset
uspto-grants-1990_03
Patent number
US04912115

Reaction notes

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