Nitric Acid → HCID 14580316, compound

HRID 1905395Notes

Reaction equation

HRID 1905395 reaction equation
[N+]([O-])(O)=O.[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[CH:20]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH3:30])[NH:23][C:22]([CH3:31])=[C:21]1[C:32]([O:34][CH3:35])=[O:33].N([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[CH3:30][C:24]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:20]([C:12]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7][CH2:6][Br:5])[C:21]([C:32]([O:34][CH3:35])=[O:33])=[C:22]([CH3:31])[N:23]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 14554057Dimethyl 4[(4-bromobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 14580316HCID 14580316, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 140 ml of 50% dioxane-water solution was added 12.8 ml conc. nitric acid (d=1.40), and suspended therein 20 g of dimethyl 4[(4-bromobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate while maintaining the system at 5° to 10° C. under ice cooling. After adding 5.6 g of sodium nitrite, the reaction mixture was vigorously stirred and then filtered. The filtrate obtained was adjusted to pH8 with a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. After washing with water, the organic layer was dried over anhydrous magnesium sulfate and the solvent distilled off. The resultant residue was recrystallized from ethyl acetate--ether to yield 10.4 g of dimethyl 2,6-dimethyl-4-[(4-bromobutoxy)-5-nitrophenyl]pyridine-3,5-dicarboxylate.

Workup

  1. filtrationfiltered
  2. customThe filtrate obtained
  3. extractionextracted with chloroform
  4. washAfter washing with water
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent distilled off
  7. customThe resultant residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9059ac8f6c1c4b048b430704e22d0d9c
Source dataset
uspto-grants-1989_06
Patent number
US04843085

Reaction notes

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