2-Chloro-3-pyridylamine → HCID 135626388, compound

HRID 637458Notes

Reaction equation

HRID 637458 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=O.[NH2:18][C:19]1[C:20](Cl)=[N:21][CH:22]=[CH:23][CH:24]=1>C(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]2[C:3]3[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=3[NH:1][C:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 805282-Chloro-3-pyridylamineHCID 122064592-Amino-4'-methoxybenzophenone

Product 1

HCID 135626388HCID 135626388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 20.0 g (0.088 mole) of 2-amino-4'-methoxybenzophenone and 13.0 g (0.097 mole) of 3-amino-2-chloropyridine (96%) was heated at 180° C. under a nitrogen atmosphere for 2.0 hr. The reaction mixture was cooled to approximately 70° C. and 100 ml of methylene chloride was added slowly. After the mixture had cooled to room temperature, another 50 ml of methylene chloride was added and the mixture was stirred overnight. The suspended solid was collected by filtration, air dried, dissolved in methanol and basified with 3N sodium hydroxide. The suspension was diluted with 500 ml water and extracted with three 250 ml portions of methylene chloride. The combined methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure. Analysis by mass spectra (EI and CI) indicated the residue was a mixture of [2-[(3-amino-2-pyridyl)amino]phenyl](4-methoxyphenyl)methanone and the title compound. The residue-mixture was dissolved in 250 ml toluene with a catalytic amount of para toluene sulfonic acid and the solution was refluxed overnight under a nitrogen atmosphere while separating water in a Dean-Stark trap. The reaction mixture was filtered while hot. The product precipitated as the filtrate cooled to room temperature and was collected by filtration. After recrystallization from benzene the product weighed 1.8 g, m.p. 198.5°-200.5° C. (d).

Workup

  1. temperatureThe reaction mixture was cooled to approximately 70° C.
  2. temperatureAfter the mixture had cooled to room temperature
  3. filtrationThe suspended solid was collected by filtration, air
  4. customdried
  5. dissolutiondissolved in methanol and basified with 3N sodium hydroxide
  6. additionThe suspension was diluted with 500 ml water
  7. extractionextracted with three 250 ml portions of methylene chloride
  8. dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. additiona mixture of [2-[(3-amino-2-pyridyl)amino]phenyl](4-methoxyphenyl)methanone
  11. dissolutionThe residue-mixture was dissolved in 250 ml toluene with a catalytic amount of para toluene sulfonic acid
  12. temperaturethe solution was refluxed overnight under a nitrogen atmosphere
  13. customwhile separating water in a Dean-Stark trap
  14. filtrationThe reaction mixture was filtered while hot
  15. customThe product precipitated as the filtrate
  16. temperaturecooled to room temperature
  17. filtrationwas collected by filtration
  18. customAfter recrystallization from benzene the product

Sources & evidence

ORD record
ord-a5368e71ac594d9eae8fcd17e1a62aa8
Source dataset
uspto-grants-1985_12
Patent number
US04556667

Reaction notes

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