Dimethylformamide → HCID 178503556, compound

HRID 1881768Notes

Reaction equation

HRID 1881768 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]#[N:15])=[C:7]([OH:13])[N:8]=[C:9]2[SH:12])=[CH:4][CH:3]=1.[CH3:16]N(C=O)C.[OH-].[Na+].IC>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]#[N:15])=[C:7]([OH:13])[N:8]=[C:9]2[S:12][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178510525HCID 178510525, compound

Product 1

HCID 178503556HCID 178503556, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

To a 50 mL round bottom flask was added 7-fluoro-3-hydroxy-1-mercaptoisoquinoline-4-carbonitrile (400 mg, 2.27 mmol), DMF (10 mL), NaOH (10 mL, 2 N), followed by iodomethane (322 mg, 2.27 mmol). After stirring for 2 h, the solution was diluted with a solution of citric acid (200 mL, 10% w/v) and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and filtered. The solvent was concentrated to yield 7-fluoro-3-hydroxy-1-(methylthio)isoquinoline-4-carbonitrile (420 mg, 1.79 mmol, 79%) as a pale yellow solid which was suitably clean for the next step. LC/MS m/z 235 [M+H].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-7239212928954809aa6f222e2466e23c
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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