Sodium ethoxide → HCID 86683194, compound

HRID 1852111Notes

Reaction equation

HRID 1852111 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](F)=[CH:9][CH:10]=2)[C:5]([O:13][CH3:14])=[CH:4][N:3]=1.[CH3:15][CH2:16][O-:17].[Na+]>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:16][CH3:15])=[CH:9][CH:10]=2)[C:5]([O:13][CH3:14])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 86683191HCID 86683191, compound

Product 1

HCID 86683194HCID 86683194, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-chloro-6-fluoro-4-methoxyisoquinoline (533 mg, 2.52 mmol) was dissolved in DMSO (5 mL) then NaOEt (171 mg, 2.52 mmol) was added to the solution. The reaction was stirred for 16 h. The reaction was diluted with EtOAc and washed with 1N HCl, then brine. The organic layer was collected, dried over sodium sulfate and concentrated under vacuum. The crude material was purified by silica gel chromatography using DCM as eluent. The product fractions were collected and solvent was removed under vacuum to give 1-chloro-6-ethoxy-4-methoxyisoquinoline (320 mg, 54% yield). MS m/z 238.0 (M++1).

Workup

  1. washwashed with 1N HCl
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude material was purified by silica gel chromatography
  6. customThe product fractions were collected
  7. customsolvent was removed under vacuum

Sources & evidence

ORD record
ord-32e5442e760e4aeba7bc5619a78ba25b
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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