HCID 19370400, compound → 100561-24-8

HRID 2248470Notes

Reaction equation

HRID 2248470 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:19][CH:9]2[CH2:10][NH:11][C:12]3[CH:13]=[CH:14][C:15]([C:16]([NH2:18])=[O:17])=[C:7]([C:8]=32)[CH2:6]1)[CH2:2][CH3:3]>ClCCCl.C(O)(=O)C.[O-2].[O-2].[Mn+4]>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:19][C:9]2=[CH:10][NH:11][C:12]3[CH:13]=[CH:14][C:15]([C:16]([NH2:18])=[O:17])=[C:7]([C:8]=32)[CH2:6]1)[CH2:21][CH3:22]

Participants

5

Reactant 1

HCID 19370400HCID 19370400, compound

Product 1

HCID 60845100561-24-8Yield 97.5%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalyst4×HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent2×

Procedure

Manganese dioxide (43.3 g, 498 m moles) was suspended in 1,2-dichloroethane (400 ml) in a 2-liter flask. The manganese dioxide suspension was cooled to -5° C., and acetic acid was added to the flask (300 ml). The manganese dioxide suspension was again cooled to -5° C. 4-(di-n-propyl)amino-6-aminocarbonyl-1,2,2a,3,4,5-hexahydrobenz[cd]indole (100 g, 332 m moles) was dissolved in acetic acid (300 ml). The solution was added to the manganese dioxide suspension while the temperature was maintained between -6° and 0° C. The reaction mixture was stirred for 2.5 hours. Filter aid (45 g) was added to the reaction mixture, which was then filtered. The filter cake was washed with acetic acid (600 ml) and dichloroethane (800 ml). The filtrate was evaporated in vacuo. The residue was taken up in toluene (500 ml), and the solution was evaporated in vacuo. The residue was again taken up in toluene (500 ml), and the solution was evaporated in vacuo. To the residue (186 g) was added aqueous sodium hydroxide (2.0 N, 700 ml). The mixture was stirred for 30 minutes, and filter aid (45 g) was added to the mixture. The mixture was filtered, and the filter cake was washed with 1,2-dichloroethane (500 ml). The organic phase of the filtrate was washed with water (700 ml), washed with saturated sodium chloride (700 ml), and then dried over sodium sulfate. The solvent was evaporated in vacuo to afford 96.8 g of the desired compound which was identified by comparison of nmr spectrum with the known compound.

Workup

  1. temperaturewas maintained between -6° and 0° C
  2. filtrationFilter aid (45 g)
  3. additionwas added to the reaction mixture, which
  4. filtrationwas then filtered
  5. washThe filter cake was washed with acetic acid (600 ml) and dichloroethane (800 ml)
  6. customThe filtrate was evaporated in vacuo
  7. customthe solution was evaporated in vacuo
  8. customthe solution was evaporated in vacuo
  9. additionTo the residue (186 g) was added aqueous sodium hydroxide (2.0 N, 700 ml)
  10. stirringThe mixture was stirred for 30 minutes
  11. filtrationfilter aid (45 g)
  12. additionwas added to the mixture
  13. filtrationThe mixture was filtered
  14. washthe filter cake was washed with 1,2-dichloroethane (500 ml)
  15. washThe organic phase of the filtrate was washed with water (700 ml)
  16. washwashed with saturated sodium chloride (700 ml)
  17. dry with materialdried over sodium sulfate
  18. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b168dbe794634a7daa116c1026779a73
Source dataset
uspto-grants-1991_08
Patent number
US05039820

Reaction notes

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