Nitric Acid → 4-Methyl-2-nitroindane-1,3-dione

HRID 1578450Notes

Reaction equation

HRID 1578450 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[CH2:5][C:6]2=[O:11].[N+:13]([O-])([OH:15])=[O:14]>CCOCC>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[CH:5]([N+:13]([O-:15])=[O:14])[C:6]2=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 205439124-Methyl-1,3-indanedione

Product 1

HCID 215030234-Methyl-2-nitroindane-1,3-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of 4-methyl-1,3-indanedione (1.02g.0.006 mole) in anhydrous ether (5 ml) at ca 10°C was added dropwise and with stirring fuming nitric acid (2.0 ml). After 10 mins. a clear, dark solution formed followed by precipitation of a bright yellow solid. The mass was filtered and washed with 5N hydrochloric acid. Recrystallisation from water/hydrochloric acid afforded the title compound, m.p. 108°-9°C. (Found; C, 56.16; H, 3.74; N, 6.32; C10H7NO4.1/2H2O requires; C, 56.07; H, 3.76; N, 6.54%).

Workup

  1. additionwas added dropwise
  2. customa clear, dark solution formed
  3. customfollowed by precipitation of a bright yellow solid
  4. filtrationThe mass was filtered
  5. washwashed with 5N hydrochloric acid
  6. customRecrystallisation from water/hydrochloric acid

Sources & evidence

ORD record
ord-e463424a48ee4eb7b0c6573933abd6ec
Source dataset
uspto-grants-1976_02
Patent number
US03936504

Reaction notes

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