HCID 18937855, compound → HCID 21847050, compound

HRID 1489501Notes

Reaction equation

HRID 1489501 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[N+:18]([O-])=O>C(O)(=O)C.[Fe]>[NH2:18][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 18937855HCID 18937855, compound

Product 1

HCID 21847050HCID 21847050, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent3×

Conditions

Temperature
70 °C

Procedure

56.9 g (1.065 mol) of iron powder in 200 ml of glacial acetic acid were initially taken and were heated to 70° C. while stirring, and a solution of 100 g (0.355 mol) of diethyl 6-methyl-5-nitropyridine-2,3-dicarboxylate (EP 277 932) in 700 ml of glacial acetic acid was added in the course of 20 minutes. Stirring was carried out for 2 hours, after which a further 25.2 g (0.45 mol) of iron powder in 200 ml of glacial acetic acid were added and stirring was continued for a further hour at 70° C. The mixture was cooled to 25° C., the precipitate was filtered off with suction and the filtrate was evaporated down under reduced pressure, after which the residue was taken up in methylene chloride, extracted in succession with water, saturated sodium bicarbonate solution and sodium chloride solution, dried over magnesium sulfate and filtered off with suction over a suction filter containing silica gel. 49 g (55% of theory) of the title compound were isolated as a yellow resin from fractions 3 and 4 after they had been evaporated down.

Workup

  1. stirringStirring
  2. stirringstirring
  3. waitwas continued for a further hour at 70° C
  4. temperatureThe mixture was cooled to 25° C.
  5. filtrationthe precipitate was filtered off with suction
  6. customthe filtrate was evaporated down under reduced pressure
  7. extractionextracted in succession with water, saturated sodium bicarbonate solution and sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered off with suction over a suction
  10. filtrationfilter
  11. additioncontaining silica gel

Sources & evidence

ORD record
ord-8bc3ebe55bbf438a9fda2b266d73bceb
Source dataset
uspto-grants-1997_10
Patent number
US05679622

Reaction notes

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