Hydrochloric Acid → 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[C:7]([C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([C:23]#N)=[CH:11][N:10]=1)=[O:8])[CH3:2].[OH-:28].[Na+].Cl.C[OH:32]>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[C:7]([C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([C:23]([OH:32])=[O:28])=[CH:11][N:10]=1)=[O:8])[CH3:2]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
To the suspension of 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (from example 82) (2.0 g, 5.52 mmol) in methanol (120 mL) was added 25% of aqueous sodium hydroxide solution (30 mL, 190 mmol). The mixture was stirred at 100° C. for 12 h more. After cooling to room temperature, the reaction was adjusted to pH=2 with 2 N HCl solution. The product was extracted with chloroform (2×200 mL). The combined organic layers were washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give solid. Recrystallization from ethanol and ether to afford 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid yellow solid. LC/MS m/e calcd for C21H19NO6 (MH+) 382,
Workup
- temperatureAfter cooling to room temperature
- extractionThe product was extracted with chloroform (2×200 mL)
- washThe combined organic layers were washed with water (3×50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give solid
- customRecrystallization from ethanol and ether
Sources & evidence
- ORD record
- ord-7cdfef953fc84b369b4b5ab0d7fcc716
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067529B2
Reaction notes
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