Trichloroacetic Acid → HCID 13280950, compound

HRID 1903637Notes

Reaction equation

HRID 1903637 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[CH2:20][NH:19][C:18](=[O:21])[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[CH:20]([OH:27])[NH:19][C:18](=[O:21])[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 145981Ro 22-8515HCID 516892Sodium BicarbonateHCID 178418268HCID 178418268, compound

Product 1

HCID 13280950HCID 13280950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In one portion, 0.35 g (1 mmol) of 8-chloro-6-(2-chlorophenyl)-1,4-dihydropyrrolo[3,4-d][2]benzazepin-3(2H)-one was added to an ice-cooled solution of 1.3 g (7.9 mmol) of trichloroacetic acid and 1.0 g (2.2 mmol) of lead tetraacetate in 15 ml of methylene chloride. After stirring for 4 hours, 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)-1,4-dihydro-1-hydroxypyrrolo[3,4-d][2]benzazepin-3(2H)-one as pale yellow prisms, mp 247°-249° 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-9bd7a700c502463cb6d6c53e10f9e87d
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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