2-Amino-4'-chlorobenzophenone → 6-(4-Chlorophenyl)-11H-pyrido[2,3-b][1,4]benzodiazepine

HRID 637456Notes

Reaction equation

HRID 637456 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.[NH2:17][C:18]1[C:19](Cl)=[N:20][CH:21]=[CH:22][CH:23]=1>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]2[C:3]3[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=3[NH:1][C:19]3[N:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 761662-Amino-4'-chlorobenzophenoneHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 1356263936-(4-Chlorophenyl)-11H-pyrido[2,3-b][1,4]benzodiazepineYield 8.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 23.2 g (0.10 mole) of 2-amino-4'-chlorobenzophenone and 14.7 g (0.11 mole) of 3-amino-2-chloropyridine (96%) were heated for 1.5 hr at 180° C. under nitrogen atmosphere. The mixture was cooled to room temperature and methylene chloride added. After stirring for 30 min., solids were separated by filtration and triturated in hot 190 proof ethanol. The remaining insoluble material was collected by filtration and recrystallized from benzene-isooctane to give 2.7 g product, m.p. 203°-204.5° C. Drying conditions prior to analyses were: overnight at 97°-98° C./0.1 mm Hg.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customsolids were separated by filtration
  3. customtriturated in hot 190 proof ethanol
  4. filtrationThe remaining insoluble material was collected by filtration
  5. customrecrystallized from benzene-isooctane

Sources & evidence

ORD record
ord-b525a9ed9bd34838b2c385e64d05a04f
Source dataset
uspto-grants-1985_12
Patent number
US04556667

Reaction notes

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