Sodium Bicarbonate → HCID 86716096, compound

HRID 627533Notes

Reaction equation

HRID 627533 reaction equation
C[O-].[Na+].[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[N:11]=[C:10](Cl)[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)=[C:8]2[Cl:24].[C:25]([O-])(O)=[O:26].[Na+]>C1(C)C=CC=CC=1>[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[N:11]=[C:10]([O:26][CH3:25])[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)=[C:8]2[Cl:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 867160976-Bromo-2,4-dichloro-3-(3-fluorophenyl)-8-methylquinoline2×

Product 1

HCID 86716096HCID 86716096, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium methoxide (4.29 g, 79.5 mmol) was added to a suspension of 6-bromo-2,4-dichloro-3-(3-fluorophenyl)-8-methylquinoline (3.06 g, 7.95 mmol, Intermediate 50, step c) in toluene (30 mL) in a pressure tube. The vessel was sealed and was heated in a 100° C. oil bath for 24 hours. To the mixture was added 10 wt. % aqueous NaHCO3 (60 mL), the mixture was stirred for several minutes, and the phases were separated. The organic phase was washed once with saturated aqueous NaCl. The organic phase was dried (Na2SO4), filtered, and concentrated to yield the title compound as a light yellow solid.

Workup

  1. customThe vessel was sealed
  2. customthe phases were separated
  3. washThe organic phase was washed once with saturated aqueous NaCl
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a7ffa9cb0d434aebbdc5812755401565
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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