Hydrochloric Acid → HCID 84660332, compound

HRID 2277596Notes

Reaction equation

HRID 2277596 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][N:7](C(=O)C(F)(F)F)[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][NH:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86685926HCID 86685926, compound

Product 1

HCID 84660332HCID 84660332, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(6-chloro-7-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoroethanone (400 mg) in MeOH (15 mL) was added K2CO3 (572 mg, 4 mmol) in H2O (10 mL). The resulting reaction mixture was stirred at room temperature for 2 hours before it was acidified with HCl (1N) to pH 8. It was then extracted with EtOAc and the organic layer was washed with H2O (2×25 mL), dried over anhy. Na2SO4, filtered and concentrated in vacuo to tive the crude title product together with a regioisomer (170 mg). Prep-TLC separation (30% EtOAc in petroleum ether) then gave the desired title compound (130 mg) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. extractionIt was then extracted with EtOAc
  3. washthe organic layer was washed with H2O (2×25 mL)
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customPrep-TLC separation (30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-60eb6aff30df4b34a8cbc58ff9431004
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…