2-Chloro-3-nitropyridine → 2-Chloro-2'-methyl-4-(3-nitro-2-pyridylamino)benzophenone

HRID 2303285Notes

Reaction equation

HRID 2303285 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:26]=[CH:25][C:15]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[O:17])=[C:14]([Cl:27])[CH:13]=1>C([O-])(O)=O.[Na+].CCOC(C)=O>[Cl:27][C:14]1[CH:13]=[C:12]([NH:11][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:26]=[CH:25][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[O:17]

Participants

5

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 10988565(4-amino-2-chlorophenyl)(2-methylphenyl)Methanone2×

Product 1

HCID 101558552-Chloro-2'-methyl-4-(3-nitro-2-pyridylamino)benzophenone

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-3-nitro-pyridine (0.32 g, 2.0 mmol) and 4-amino-2-chloro-2′-methylbenzophenone (compound 2) (0.49 g, 2.0 mmol) was mixed thoroughly. The reaction mixture was warmed at 100° C. for 0.5 h and then at 160° C. for 0.5 h. The reaction mixture was cooled to room temperature, and dissolved in saturated aqueous NaHCO3 (10 mL) and EtOAc (30 mL). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (10 mL), dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe phases were separated
  3. washthe organic phase was washed with saturated aqueous NaHCO3 (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1ea0df6416d45fb92efe078ad33becf
Source dataset
uspto-grants-2002_08
Patent number
US06432962B1

Reaction notes

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