HCID 13271775, compound → HCID 135759062, compound

HRID 464581Notes

Reaction equation

HRID 464581 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[CH:6]3[C:20](=[O:21])[NH:19][CH:18]=[N:17][CH:7]3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:20](=[O:21])[NH:19][CH:18]=[N:17][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 13271775HCID 13271775, compound

Product 1

HCID 135759062HCID 135759062, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.2 g (6.8 mmol) of 9-chloro-4a,11b-dihydro-7-phenyl-5H-pyrimido[4,5-d][2]benzazepin-1(2H)-one and 10 g (110 mmol) of activated manganese dioxide in 100 mL of tetrahydrofuran was refluxed for 18 hr. The mixture was cooled, the manganese dioxide was removed by filtration over celite and the filtrate was concentrated at reduced pressure. Purification of the residue by column chromatography (silica gel 10 g; eluents, 20% ether in methylene chloride followed by 50% ethyl acetate in methylene chloride) gave pale yellow prisms, mp 226°-229°.

Workup

  1. temperaturewas refluxed for 18 hr
  2. temperatureThe mixture was cooled
  3. customthe manganese dioxide was removed by filtration over celite
  4. concentrationthe filtrate was concentrated at reduced pressure
  5. customPurification of the residue by column chromatography (silica gel 10 g; eluents, 20% ether in methylene chloride followed by 50% ethyl acetate in methylene chloride)
  6. customgave pale yellow prisms, mp 226°-229°

Sources & evidence

ORD record
ord-f2daba415c84409f83f44ee502849fea
Source dataset
uspto-grants-1985_10
Patent number
US04548750

Reaction notes

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