Acetamide → HCID 89644412, compound

HRID 1746842Notes

Reaction equation

HRID 1746842 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]([F:16])([F:15])[F:14])[CH:8](Cl)[NH:7][CH:6]=[CH:5]2.C([NH2:21])(=O)C.C([O-])([O-])=O.[K+].[K+]>C(OC(=O)C)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]([F:16])([F:15])[F:14])[C:8]([NH2:21])=[N:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 89644080HCID 89644080, compound

Product 1

HCID 89644412HCID 89644412, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

4 g (12 mmol) of 6-Bromo-1-chloro-7-trifluoromethoxy-2H-isoquinoline are intermixed with 14 g acetamide (14 eq.) and 5 g (3 eq.) K2CO3. This mixture is heated for 1 h at 180° C. under stirring. The reaction mixture is stirred in ethylacetate (100 ml) and water (100 ml). The organic phase is separated, dried with Na2SO4 and the solvent removed under reduced pressure after filtration of the drying agent. For purification, a chromatography on silical gel (40-63μ, Merck) is performed with ethylacetate as mobile phase. 890 mg of a solid are obtained.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried with Na2SO4
  3. customthe solvent removed under reduced pressure
  4. filtrationafter filtration of the drying agent
  5. customFor purification

Sources & evidence

ORD record
ord-76f2430b7d15484bbb2db50e1e718941
Source dataset
uspto-grants-2015_10
Patent number
US09150544B2

Reaction notes

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