Sulfuric Acid → 1,3(2H,4H)-Isoquinolinedione, 7-amino-4,4-dimethyl-8-nitro-

HRID 1634223Notes

Reaction equation

HRID 1634223 reaction equation
C([NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]2[C:8]([C:9]([CH3:21])([CH3:20])[C:10](=[O:19])[NH:11][C:12]2=[O:18])=[CH:7][CH:6]=1)(=O)C.OS(O)(=O)=O>>[NH2:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]2[C:8]([C:9]([CH3:21])([CH3:20])[C:10](=[O:19])[NH:11][C:12]2=[O:18])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 118331714,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione2×

Product 1

HCID 111184431,3(2H,4H)-Isoquinolinedione, 7-amino-4,4-dimethyl-8-nitro-Yield 99%

Conditions

Temperature
70 °C

Procedure

The above amide was converted to 7-acetamido-4,4-dimethyl-8-nitro-2H,4H-isoquinoline-1,3-dione as described in U.S. Pat. No. 4176184 (1979). 7-Acetamido-4,4-dimethyl-8-nitro-2H,4H-isoquinoline-1,3-dione (4.0 g, 13.7 mmol) was added to 90% H2SO4 and heated at 70° C. for 8 h. The cooled mixture was poured onto ice. The precipitate was collected, dissolved in ethyl acetate, washed with water, dried and evaporated to give 7-amino-4,4-dimethyl-8-nitro-2H,4H-isoquinoline-1,3-dione (3.38 g, 99%), mp 259-263° C.; MS (CI) 250 (MH+).

Workup

  1. additionThe cooled mixture was poured onto ice
  2. customThe precipitate was collected
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-78a25eaa7da44e99a8f8565b757c1253
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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