Dichloromethane → [2-[(3-Amino-2-pyridinyl)amino]-4-chlorophenyl]phenylmethanone

HRID 543603Notes

Reaction equation

HRID 543603 reaction equation
[NH2:1][C:2]1[CH:16]=C[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](Cl)=[CH:8][CH:7]=1)=[O:5].[NH2:17][C:18]1[C:19](Cl)=[N:20][CH:21]=[CH:22][CH:23]=1.[CH2:25]([Cl:27])Cl>>[NH2:17][C:18]1[C:19]([NH:1][C:2]2[CH:16]=[C:25]([Cl:27])[CH:14]=[CH:13][C:3]=2[C:4]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:5])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 761662-Amino-4'-chlorobenzophenoneHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 15586654[2-[(3-Amino-2-pyridinyl)amino]-4-chlorophenyl]phenylmethanone

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 23.2 g (0.1 mole) of 2-amino-4'-chlorobenzophenone and 14.2 g (0.11 mole) of 3-amino-2-chloropyridine was heated at 180° C. under nitrogen atmosphere for 2.5 hr. The mixture solidifed upon cooling to room temperature and was broken up with a spatula. The solid was suspended in 100 ml of methylene chloride and collected by filtration. The filter cake was dissolved in a mixture of water-methanol, basified with 3 N sodium hydroxide and extracted twice with methylene chloride. The combined methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure. The residue which had crystallized was triturated in isopropyl ether and the solid (16.7 g) collected by filtration. A 3 g sample was recrystallized from isopropyl ether to give 1.6 g product; m.p. 153°-155° C.

Workup

  1. temperatureupon cooling to room temperature
  2. filtrationcollected by filtration
  3. dissolutionThe filter cake was dissolved in a mixture of water-methanol
  4. extractionextracted twice with methylene chloride
  5. dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue which had crystallized
  8. customwas triturated in isopropyl ether
  9. filtrationthe solid (16.7 g) collected by filtration
  10. customA 3 g sample was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-06baa884e0cf491d9562bc1181fb8948
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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