Sulfuric Acid → HCID 18670448, compound

HRID 1059385Notes

Reaction equation

HRID 1059385 reaction equation
[CH3:1][C:2]([C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:26])[CH2:3][CH2:4][CH2:5][C:6]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1)(C(OCC)=O)C(OCC)=O.S(=O)(=O)(O)O.[Cl-].[Na+]>C(O)C>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:1])([CH3:26])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:18][CH:19]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 18670226HCID 18670226, compound

Product 1

HCID 18670448HCID 18670448, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.71 g of triethyl 5-methyl-1-(5-nitropyridin-2-yl)hexane-1,1,5-tricarboxylate was treated in the same manner as the one of Production Example 149 to thereby give 2.87 g of a yellow oily substance. A 1.82 g portion of this product was dissolved in 30 ml of ethanol. After adding 3 ml of conc. sulfuric acid, the resulting mixture was heated under reflux for 7 hours. After the completion of the reaction, the reaction mixture was poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and filtered. The filtrate was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 1.0 g of the title compound as a yellow oily substance.

Workup

  1. customto thereby give 2.87 g of a yellow oily substance
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 7 hours
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationThe filtrate was distilled under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-2812a39189de4d58932c1fb0f912ba17
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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