Lithium Hydroxide → HCID 67491743, compound

HRID 711063Notes

Reaction equation

HRID 711063 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=2)[CH:6]=[CH:5][N:4]=1.[OH-].[Li+]>CO.Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 674914067-Isoquinolinecarboxylic acid, 1-methoxy-, methyl ester

Product 1

HCID 67491743HCID 67491743, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-methoxyisoquinoline-7-carboxylate (443 mg, 2.04 mmol) in methanol (10 mL) was added 2 N aqueous lithium hydroxide (20 mL). The reaction was stirred at room temperature for 24 hours. The reaction mixture was diluted with 1 N aqueous hydrochloric acid and ethyl acetate. The layers were separated and the aqueous was extracted two more times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound (414 mg, 100%) as a solid. +ESI (M+H) 204.1; 1H NMR (400 MHz, DMSO-d6, δ): 13.24 (s, 1H), 8.76 (d, J=0.8 Hz, 1H), 8.18 (dd, J=8.6, 1.8 Hz, 1H), 8.11 (d, J=5.9 Hz, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.45 (d, J=5.9 Hz, 1H), 4.07 (s, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted two more times with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5646ef0b734b4d349eb99868bac13a3a
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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