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2-Amino-4'-chlorobenzophenone → (4-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone

HRID 1633365
Notes
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Reaction equation

HRID 1633365 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][C:9]([Cl:12])=[CH:8][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>C1(C)C=CC=CC=1>[Cl:12][C:9]1[CH:10]=[CH:11][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:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 761662-Amino-4'-chlorobenzophenoneHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 13388387(4-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanoneYield 56.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Under nitrogen atmosphere, 50.0 g (0.216 mole) of 2-amino-4'-chlorobenzophenone was added in four portions at 15 min intervals to a stirred melt (105°-110° C.) of 35.9 g (0.227 mole) of 2-chloro-3-nitropyridine. The reaction temperature was increased to 120° C. for 3 hr and then to 150° C. for 2 hr. The stirred mixture was cooled to 115° C. and 100 ml of hot toluene was added. The cooled mixture (room temperature) was filtered. The filtrate was washed with 75 ml of 5% sodium hydroxide solution, 50 ml of water and 30 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from ethyl acetate-isopropyl ether to give 43 g (56.4%) solid. Recrystallization from ethyl acetate-isopropyl ether gave 18.26 g* of bright-yellow solid, m.p. 138'-140° C.

Workup

  1. temperatureThe stirred mixture was cooled to 115° C.
  2. filtrationThe cooled mixture (room temperature) was filtered
  3. washThe filtrate was washed with 75 ml of 5% sodium hydroxide solution, 50 ml of water and 30 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-5a9cb259bb9044afb88e53cce2077d22
Source dataset
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04480100

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes