Hydrochloric Acid → (3-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone

HRID 1633354Notes

Reaction equation

HRID 1633354 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5].Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.Cl>>[Cl:12][C:8]1[CH:7]=[C:6]([C:4]([C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[NH:1][C:18]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:5])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 796132-Chloro-3-nitropyridineHCID 12231012Methanone, (2-aminophenyl)(3-chlorophenyl)-

Product 1

HCID 13388385(3-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanoneYield 29.9%

Conditions

Temperature
125 °C

Procedure

To a stirred melt of 10.0 g (0.043 mole) of 2-amino-3'-chlorobenzophenone under an atmosphere of nitrogen gas was added at 115°-120° C. in two portions at 20 min intervals, 6.3 g (0.040 mole) of 2-chloro-3-nitropyridine. The reaction mixture was heated at 125° C. for 4 hr and then poured into 250 ml of hot 3N hydrochloric acid under vigorous agitation. The mixture was cooled, the aqueous portion decanted and the residue was dissolved in 150 ml of methylene chloride. The methylene chloride solution was washed in sequence five times with 30 ml portions of 3N hydrochloric acid, once with 30 ml of 5% aqueous sodium hydroxide, once with 30 ml of saturated aqueous sodium chloride solution. The washed methylene chloride solution was dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from isopropyl ether, yielding 4.23 g (28%) of dark yellow solid, m.p. 124°- 125° C.

Workup

  1. temperatureThe mixture was cooled
  2. customthe aqueous portion decanted
  3. dissolutionthe residue was dissolved in 150 ml of methylene chloride
  4. washThe methylene chloride solution was washed in sequence five times with 30 ml portions of 3N hydrochloric acid, once with 30 ml of 5% aqueous sodium hydroxide, once with 30 ml of saturated aqueous sodium chloride solution
  5. dry with materialThe washed methylene chloride solution was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-a5bd325772704fac8cf954e44c84506f
Source dataset
uspto-grants-1984_10
Patent number
US04480100

Reaction notes

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