p-Toluidine → HCID 57671808, compound

HRID 871986Notes

Reaction equation

HRID 871986 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[NH:8]2.[CH3:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[F:22][C:20]1[CH:19]=[CH:18][C:17]([O:23][CH3:24])=[C:16]([C:4]2[C:3]([CH2:2][NH:30][C:29]3[CH:31]=[CH:32][C:26]([CH3:25])=[CH:27][CH:28]=3)=[C:12]3[C:7]([NH:8][C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[NH:11]3)=[CH:6][CH:5]=2)[CH:21]=1

Participants

7

Reactant 4

HCID 7813p-ToluidineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57671966HCID 57671966, compound

Product 1

HCID 57671808HCID 57671808, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-chloromethyl-7-(5-fluoro-2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 4-2, 50.7 mg, 0.15 mmol), 4-methylaniline (19.3 mg, 0.18 mmol), and potassium carbonate (60.6 mg, 0.44 mmol) was suspended in anhydrous N,N-dimethylformamide (1 mL) and stirred at 80° C. overnight. After cooling down, ethyl acetate (30 mL) and water (30 mL) were added and partitioned. The organic layer was washed with water (30 mL) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (48.2 mg) as a pale yellow solid. (Yield 80%)

Workup

  1. temperatureAfter cooling down
  2. custompartitioned
  3. washThe organic layer was washed with water (30 mL) and saturated brine (30 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4e386ad07c0245ee8a4cf9e821dfc2ba
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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