Potassium Hydroxide → 1-(Methylamino)isoquinoline-6-carboxylic acid
Reaction equation
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]CC)=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[OH-].[K+]>C(O)C>[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a suspension of ethyl 1-(methylamino)isoquinoline-6-carboxylate (150 mg, 0.65 mmol) in ethanol (2.5 mL) was added 1 N aqueous potassium hydroxide (6.5 mL, 6.5 mmol). The reaction was heated to 65° C. for 1.5 hours. The reaction was cooled to room temperature and concentrated to dryness. The solid was dissolved in water and the solution was acidified with 1 N HCl. The mixture was concentrated. The solid was dissolved in water (50 mL) and extracted twice with 2-butanol (50 mL). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered, and concentrated to give the title compound (95 mg, 72%) as a white solid. +ESI (M+H) 203.2; 1H NMR (400 MHz, DMSO-d6, δ): 13.07 (br.s., 1H), 10.25 (d, J=4.9 Hz, 1H), 8.74 (d, J=8.8 Hz, 1H), 8.51 (s, 1H), 8.15 (dd, J=8.6, 1.8 Hz, 1H), 7.67 (d, J=6.8 Hz, 1H), 7.35 (d, J=7.0 Hz, 1H), 3.15 (d, J=4.7 Hz, 3H).
Workup
- temperatureThe reaction was cooled to room temperature
- concentrationconcentrated to dryness
- dissolutionThe solid was dissolved in water
- concentrationThe mixture was concentrated
- dissolutionThe solid was dissolved in water (50 mL)
- extractionextracted twice with 2-butanol (50 mL)
- washThe combined organics were washed with brine (20 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7984b8b6734f48a091d693c8c29e5c23
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181252B2
Reaction notes
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