Hydrochloric Acid → HCID 58368670, compound

HRID 1192538Notes

Reaction equation

HRID 1192538 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH3:18])=[N:10][C:9]=2[C:19]([O:21]C)=[O:20])[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].O.Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH3:18])=[N:10][C:9]=2[C:19]([OH:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58368546HCID 58368546, compound

Product 1

HCID 58368670HCID 58368670, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(3-fluorophenyl)-1-methylisoquinoline-3-carboxylate (0.423 g, 1.43 mmol) and 3.0 M lithium hydroxide in water (2.39 mL, 7.16 mmol) in tetrahydrofuran (2.4 mL) was stirred at room temperature for 3 hours. After neutralized with 1 N HCl, the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The resulting crude acid was used directly in the next step (0.40 g, 99%). LCMS calculated for C17H13FNO2 (M+H)+: m/z=282.1; Found: 282.0.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-49e44e173c834c1dbd6299e24ad044d3
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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