Hydrochloric Acid → HCID 14209554, compound

HRID 845760Notes

Reaction equation

HRID 845760 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:43].Cl.Cl>C(Cl)Cl.C(O)C>[ClH:43].[ClH:43].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 142095531-Phenyl-3,3-bis[(pyridin-2-yl)methyl]-1,3-dihydro-2H-indol-2-one

Product 1

HCID 14209554HCID 14209554, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

8.2 g of 3,3-Bis(2-pyridylmethyl)-1-phenylindolin-2-one was converted to the dihydrochloride salt by dissolving it in 25 ml methylene chloride and adding 25 ml of 25% hydrochloric acid in ethanol. The solution was evaporated and the glassy residue was dissolved in 75 ml boiling acetone. Cooling to room temperature and trituration started crystallization. After sitting at room temperature for 6 hours, the mixture was kept at 0° overnight. The product was then filtered, washed with cold acetone and dried in a vacuum oven for 1 hour at 60° over Granusic to yield 8.55 g; m.p. 250°-251°. The product was recrystallized from isopropanol affording 8.29 g; m.p. 250°-251°.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe glassy residue was dissolved in 75 ml
  3. customcrystallization
  4. waitthe mixture was kept at 0° overnight
  5. filtrationThe product was then filtered
  6. washwashed with cold acetone
  7. customdried in a vacuum oven for 1 hour at 60° over Granusic
  8. customto yield 8.55 g
  9. customThe product was recrystallized from isopropanol affording 8.29 g

Sources & evidence

ORD record
ord-fd87c603f5cd4c9f974d09a63edcbe87
Source dataset
uspto-grants-1988_07
Patent number
US04760083

Reaction notes

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