4-Chloroaniline → HCID 14476376, compound

HRID 359113Notes

Reaction equation

HRID 359113 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.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1>C1(C)C(C)=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24](=[O:25])[N:16]2[CH2:15][CH2:14][CH2:13][N:10]2[CH2:11][CH:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 14476373HCID 14476373, compound

Product 1

HCID 14476376HCID 14476376, compoundYield 54%

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-hydroxy-1-isoindolinone (10 g) and 4-chlorophenylamine (4.6 g) in xylene (230 cc) at a temperature close to 20° C. in a Dean Stark apparatus. Agitation is continued for 6 hours at a temperature close to 135° C. After cooling to a temperature close to 20° C., the precipitate formed is filtered, washed with xylene (2×50 cc), dried under reduced pressure (20 mm Hg; 2.7 kPa) and recrystallized from boiling acetonitrile (360 cc). 7.1 g of 3-(4-chlorophenylamino)-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone are obtained, melting at 188° 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. customthe precipitate formed
  6. filtrationis filtered
  7. washwashed with xylene (2×50 cc)
  8. customdried under reduced pressure (20 mm Hg; 2.7 kPa)
  9. customrecrystallized

Sources & evidence

ORD record
ord-62b3d9e33de843c88421d4ac712c0e12
Source dataset
uspto-grants-1991_03
Patent number
US04999355

Reaction notes

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