Nitric Acid → 4,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione

HRID 47103Notes

Reaction equation

HRID 47103 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([CH3:15])=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:16])[NH:4][C:3]1=[O:17].[N+:19]([O-])([OH:21])=[O:20]>>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[C:7]([N+:19]([O-:21])=[O:20])[C:8]([NH:12][C:13]([CH3:15])=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:16])[NH:4][C:3]1=[O:17]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 135581564,4-dimethyl-7-acetamino-2H,4H-isoquinoline-1,3-dione

Product 1

HCID 118331714,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dioneYield 85%

Procedure

220 gm of 4,4-dimethyl-7-acetamino-2H,4H-isoquinoline-1,3-dione were added in portions to 800 ml of fuming nitric acid at -20° C. while stirring. The mixture was stirred for one hour at this temperature. Then, the reaction mixture was poured over ice, the precipitate was suction-filtered off, washed neutral with water, dried in the air, and boiled with isopropanol. After cooling, the crystals were suction-filtered off and washed with ether, yielding 222 gm (85% of theory) of 4,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione, m.p. 249° C. (decomp.).

Workup

  1. stirringThe mixture was stirred for one hour at this temperature
  2. additionThen, the reaction mixture was poured over ice
  3. filtrationthe precipitate was suction-filtered off
  4. washwashed neutral with water
  5. customdried in the air
  6. temperatureAfter cooling
  7. filtrationthe crystals were suction-filtered off
  8. washwashed with ether

Sources & evidence

ORD record
ord-a14458c8825d4459a0d1cea8d0e9f4b1
Source dataset
uspto-grants-1979_11
Patent number
US04176184

Reaction notes

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