Dimethylformamide → HCID 67775230, compound

HRID 533427Notes

Reaction equation

HRID 533427 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[OH:23])=[N:4][CH:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[O:23][CH3:24])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136372360HCID 136372360, compound

Product 1

HCID 67775230HCID 67775230, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-chloro-1-(3-chloro-2-hydroxyphenyl)isoquinoline-7-carboxylate (150 mg), potassium carbonate (119 mg), iodomethane (245 mg), and DMF (3 mL) was stirred at room temperature for one day. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried, and concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 4-chloro-1-(3-chloro-2-methoxyphenyl)isoquinoline-7-carboxylate (130 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7dcc0344a7e0435b95696ea1840f9b24
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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