Sodium Hydroxide → 1-(2-Fluorophenyl)isoquinoline-3-carboxylic acid

HRID 1020012Notes

Reaction equation

HRID 1020012 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([O:20]C)=[O:19])[N:9]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([OH:20])=[O:19])[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66600632HCID 66600632, compound

Product 1

HCID 132723921-(2-Fluorophenyl)isoquinoline-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 1-(2-fluorophenyl)isoquinoline-3-carboxylate (0.096 g, 0.34 mmoles) was dissolved in methanol (5 mls) followed by sodium hydroxide (1M, 0.51 mls, 0.51 mmoles) and the reaction heated (40° C.) overnight. The solution was then evaporated and the residue diluted with water (10 mls), and ethyl acetate (10 mls). This mixture was then acidified hydrochloric acid (1M HCl) to ˜pH 5.0 and the layers separated. The aqueous layer was further extracted with ethyl acetate (2×10 mls) and the organic layers combined and washed with water (10 mls) and brine (10 mls). The organic solution was evaporated to leave a white residue (0.091 mgs, 100% yield, 90% pure).

Workup

  1. customThe solution was then evaporated
  2. additionthe residue diluted with water (10 mls), and ethyl acetate (10 mls)
  3. customthe layers separated
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×10 mls)
  5. washwashed with water (10 mls) and brine (10 mls)
  6. customThe organic solution was evaporated
  7. customto leave a white residue (0.091 mgs, 100% yield, 90% pure)

Sources & evidence

ORD record
ord-9e166db4ad694ca3adc02d15bf585d22
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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