Nitric Acid → 3,3-Dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one

HRID 1088947Notes

Reaction equation

HRID 1088947 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH3:10][C:11]1([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:20]>>[CH3:10][C:11]1([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:1]([O-:4])=[O:2])[CH:18]=2)[NH:13][C:12]1=[O:20]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 154800743,3-Dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one

Procedure

A solution of 22 ml. fuming nitric acid in 200 ml. 80% sulphuric acid is added dropwise, with cooling, to a solution of 100 g. (0.62 mol) 3,3-dimethylindolin-2-one in 500 ml. 80% sulphuric acid. The reaction mixture is then stirred for about 30 minutes, poured on to ice, filtered with suction, washed with water and dried. Yield: 100 g. (78% of theory); m.p. 192°-196° C. (ethyl acetate/heptane).

Workup

  1. temperaturewith cooling, to a solution of 100 g
  2. additionpoured on to ice
  3. filtrationfiltered with suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d474ede88e7a4dfba2e567eaa37afba8
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

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