Trichloroacetic Acid → HCID 13280956, compound

HRID 1903636Notes

Reaction equation

HRID 1903636 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:20](=[O:21])[NH:19][CH2:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.ClC(Cl)(Cl)C(O)=[O:27].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:20](=[O:21])[NH:19][CH:18]([OH:27])[C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6421Trichloroacetic AcidHCID 516892Sodium BicarbonateHCID 13280954HCID 13280954, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 13280956HCID 13280956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In one portion, 0.7 g (2 mmol) of 8-chloro-6-(2-chlorophenyl)-3,4-dihydropyrrolo[3,4-d][2]benzazepin-1(2H)-one was added to an ice-cooled solution of 2.6 g (15.8 mmol) of trichloroacetic acid and 2.0 g(4.4 mmol) of lead tetraacetate in 30 ml of methylene chloride. After stirring for 1 hour, the mixture was neutralized with saturated aqueous sodium bicarbonate solution. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to a yellow residue. Purification of the residue by column chromatography (silica gel, 10 g; eluent, 5% methanol in methylene chloride) followed by crystallization from ether gave 8-chloro-6-(2-chlorophenyl)-3,4-dihydro-3-hydroxypyrrolo[3,4-d][2]benzazepin-1(2H)-one as pale yellow prisms, mp 221°-222° C.

Workup

  1. washThe methylene chloride solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure to a yellow residue
  4. customPurification of the residue by column chromatography (silica gel, 10 g; eluent, 5% methanol in methylene chloride)
  5. customfollowed by crystallization from ether

Sources & evidence

ORD record
ord-e34292fe4e094dd4aab12762270cb1e8
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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