Nitric Acid → HCID 19858077, compound

HRID 2073392Notes

Reaction equation

HRID 2073392 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1([CH3:26])[C:10](=[O:11])[O:9][C:8]2[CH:12]=[CH:13][C:14]3[C:19]([C:7]1=2)=[CH:18][C:17]([CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)=[CH:16][CH:15]=3.C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:5][C:6]1([CH3:26])[C:10](=[O:11])[O:9][C:8]2[CH:12]=[CH:13][C:14]3[C:19]([C:7]1=2)=[CH:18][C:17]([CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)=[C:16]([N+:1]([O-:4])=[O:2])[CH:15]=3

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 19811645HCID 19811645, compound

Product 1

HCID 19858077HCID 19858077, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Nitric acid (72% by weight, 0.045 ml) was added dropwise to a stirred, ice-cooled mixture of 1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone (0.44 g) and acetic anhydride (6 ml). The mixture was stirred at room temperature for 18 h, then added to a stirred mixture of aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic phase was separated, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash chromatography. Elution with ethyl acetate:pentane, 3:1 v/v, gave 1,1-dimethyl-7-nitro-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 183°-185° after recrystallisation from ethyl acetate. (Example 13).

Workup

  1. temperaturecooled
  2. customThe organic phase was separated
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customthe residue was purified by flash chromatography
  6. washElution with ethyl acetate

Sources & evidence

ORD record
ord-a9648b1c8d544a73929ff38bf12e3a62
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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