Acetonitrile → HCID 178497286, compound

HRID 533411Notes

Reaction equation

HRID 533411 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[C:4]([CH3:16])[N:3]=1.[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(#N)C>CO>[F:18][C:5]1[C:6]2[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2)[C:2]([OH:1])=[N:3][C:4]=1[CH3:16]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2724933SelectfluorHCID 178497268HCID 178497268, compound

Product 1

HCID 178497286HCID 178497286, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1-hydroxy-3-methylisoquinoline-7-carboxylate (120 mg), Selectfluor (registered trademark) (215 mg), acetonitrile (2 mL), and methanol (2 mL) was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was diluted with water. Then, the precipitate was collected by filtration to obtain methyl 4-fluoro-1-hydroxy-3-methylisoquinoline-7-carboxylate (55 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with water
  3. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-6f23a72f4efb4eca885008a77c6dbd78
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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