2-Aminobenzophenone → HCID 135626384, compound

HRID 637453Notes

Reaction equation

HRID 637453 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:16][C:17]1[C:18](Cl)=[N:19][CH:20]=[CH:21][CH:22]=1>>[C:6]1([C:4]2[C:3]3[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=3[NH:1][C:18]3[N:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 760802-AminobenzophenoneHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 135626384HCID 135626384, compoundYield 26.9%

Conditions

Temperature
190 °C

Procedure

A mixture of 19.7 g (0.1 mole) of 2-aminobenzophenone and 15.0 g (0.12 mole) of 3-amino-2-chloropyridine was heated under nitrogen atmosphere at 190° C. for 1.75 hr. The mixture was cooled to room temperature and partitioned between 3N aqueous sodium hydroxide and methylene chloride. The combined methylene chloride extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The residue, 32.7 g, was dissolved in benzene and chromatographed on a column of florisil packed in benzene, eluting with benzene and 1-2% acetone-benzene mixtures. After evaporation, the solid was crystallized from benzene to give 7.3 g product; m.p. 106°-108° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between 3N aqueous sodium hydroxide and methylene chloride
  3. washThe combined methylene chloride extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. dissolutionThe residue, 32.7 g, was dissolved in benzene
  7. customchromatographed on a column of florisil
  8. washeluting with benzene and 1-2% acetone-benzene mixtures
  9. customAfter evaporation
  10. customthe solid was crystallized from benzene

Sources & evidence

ORD record
ord-e02838f5bb664e4eb074e852627e1e95
Source dataset
uspto-grants-1985_12
Patent number
US04556667

Reaction notes

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