Nitric Acid → Nivimedone

HRID 1284305Notes

Reaction equation

HRID 1284305 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[CH2:6][C:5]2=[O:13].[N+:14]([O-])([OH:16])=[O:15]>CCOCC>[CH3:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[CH3:1])[C:5](=[O:13])[CH:6]([N+:14]([O-:16])=[O:15])[C:7]2=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15140857HCID 15140857, compound

Product 1

HCID 64753Nivimedone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5,6-dimethyl indane-1,3-dione (0.52 g; 0.003 mole) suspended in anhydrous ether (5 ml.) was stirred at 10°C during the dropwise addition of fuming nitric acid (1.0 ml.). After the addition was complete the mixture was stirred at ambient temperature for 1 hr. and the precipitated yellow solid filtered. m.p. (water, hydrochloric acid) 111°-113°C. (Found: C, 60.11; H, 4.10; N, 6.14; C11H9NO4 requires: C, 60.28; H, 4.14; N, 6.39%).

Workup

  1. additionAfter the addition
  2. filtrationand the precipitated yellow solid filtered
  3. customm.p. (water, hydrochloric acid) 111°-113°C. (Found: C, 60.11; H, 4.10; N, 6.14; C11H9NO4 requires: C, 60.28; H, 4.14; N, 6.39%)

Sources & evidence

ORD record
ord-0b59c670840140de80a10395b727c48b
Source dataset
uspto-grants-1976_08
Patent number
US03978231

Reaction notes

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