2-Aminopyridine → HCID 14476377, compound

HRID 359114Notes

Reaction equation

HRID 359114 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[CH:24]([OH:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=O)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>C1(C)C(C)=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[NH:27][CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24](=[O:25])[N:16]1[CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 104392-AminopyridineHCID 14476373HCID 14476373, compound

Product 1

HCID 14476377HCID 14476377, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 7237O-XyleneSolvent

Procedure

Para-toluenesulphonic acid (50 mg) is added to an agitated solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-3-hydroxy1-isoindolinone (6 g) and 2-aminopyridine (2 g) in xylene (150 cc) at a temperature close to 20° C. in a Dean Stark apparatus. Agitation is continued for 5 hours at a temperature close to 135° C. After cooling to a temperature close to 20° C., the solution is washed with aqueous sodium bicarbonate solution (2×100 cc) then with distilled water (2×50 cc). The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 80° C. The precipitate is recrystallized from boiling acetonitrile (45 cc). 3.7 g of 3-(2-pyridylamino)-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone are obtained, melting at 153° C.

Workup

  1. customclose to 20° C. in a Dean Stark apparatus
  2. customclose to 135° C
  3. temperatureAfter cooling to a temperature
  4. customclose to 20° C.
  5. washthe solution is washed with aqueous sodium bicarbonate solution (2×100 cc)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 80° C
  9. customThe precipitate is recrystallized

Sources & evidence

ORD record
ord-0fc9248c158045e6a781104f0073447b
Source dataset
uspto-grants-1991_03
Patent number
US04999355

Reaction notes

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