HCID 70347307, compound → HCID 70347304, compound

HRID 582598Notes

Reaction equation

HRID 582598 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([CH3:35])=[C:5]([C:22](=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][Br:33])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>ClCCl.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:5]([C:22](=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][Br:33])=[C:4]([CH3:35])[N:3]=1

Participants

4

Reactant 1

HCID 70347307HCID 70347307, compound

Product 1

HCID 70347304HCID 70347304, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

41.9 g of ethyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-(11-bromo-1-oxo-undecyl)pyridine-3-carboxylate are dissolved in 300 ml of dichloromethane and 137 g of manganese dioxide are added. The mixture is stirred at RT for 20 h, then filtered off through Celite and the filtrate is washed with water. The oil remaining after concentration of the filtrate crystallizes on standing or is seeded. It is triturated with diisopropyl ether and filtered off with suction. 23.2 g of the title compound of m.p. 73-74° C. are obtained.

Workup

  1. filtrationfiltered off through Celite
  2. washthe filtrate is washed with water
  3. customcrystallizes on standing
  4. customIt is triturated with diisopropyl ether
  5. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-8bc5f926189344e98506b4ad17a3dbb1
Source dataset
uspto-grants-1999_07
Patent number
US05925642

Reaction notes

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