Hydrochloric Acid → HCID 15230473, compound

HRID 1464297Notes

Reaction equation

HRID 1464297 reaction equation
Cl.O[C:3]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]2=[O:21].[OH-].[Na+]>C(Cl)Cl>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([CH:3]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:13])[N:8]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:7]3=[O:21])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20082012HCID 20082012, compound

Product 1

HCID 15230473HCID 15230473, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 12 ml of conc. hydrochloric acid were added 546 mg of stannous chloride and 352 mg of 5-[hydroxybis (4-chlorophenyl) methyl]-2-(3-pyridylmethyl)-1H-isoindole-1,3-dione, and the resultant mixture was stirred at 70° C. for 1.5 hours. After ice cooling, the reaction mixture was made alkaline with 1N aqueous sodium hydroxide and shaken with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (1:1) to give 188 mg of the titled compound.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe resultant residue was chromatographed on a column of silica gel
  4. washeluting with ethyl acetate and hexane (1:1)

Sources & evidence

ORD record
ord-a3f784755330490cb8e2d94d2582f4fd
Source dataset
uspto-grants-1994_04
Patent number
US05304556

Reaction notes

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