Ammonia → HCID 67980328, compound

HRID 2063938Notes

Reaction equation

HRID 2063938 reaction equation
Cl[N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C(O)(C(F)(F)F)=O.N>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:4]1[C:12](=[C:11]3[C:6]([N:5]=1)=[CH:7][CH:8]=[CH:9][CH2:10]3)[CH:3]=[N:2]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 86667267HCID 86667267, compound

Product 1

HCID 67980328HCID 67980328, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(chlorophenylquinolin-3-yl-amine (400 mg), CF3COOH (8 ml), Pd(OAc)2 (300 mg) was refluxed for 6 hr at 80° C. The reaction mixture was allowed to cool to room temperature, poured in ice cold water (15 ml), neutralized with aqueous ammonia and extracted with EtOAc (3×50 mL), washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography to yield the pure solid product (130 mg). Mp: 146-148° C. 1H-NMR: (DMSO-d6): δ 9.52 (s, 1H), 8.96 (d, 1H, J=8.1 Hz), 8.86 (d, 1H, J=1.5 Hz), 8.24 (d, 1H, J=8.1 Hz), 7.88-7.78 (m, 3H), 7.70-7.66 (dd, 1H, J=6.6, 2.1 Hz).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-56d116005189498fac33cb98c9a597a4
Source dataset
uspto-grants-2012_10
Patent number
US08288410B2

Reaction notes

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