HCID 13271775, compound → HCID 135759062, compound

HRID 2295976Notes

Reaction equation

HRID 2295976 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-c5cd879811e846538023ce8103428ff2
Source dataset
uspto-grants-1984_01
Patent number
US04427589

Reaction notes

Loading…