Acetic Acid → 8-amino-3,4-dimethyl-7-nitro-2H-isoquinolin-1-one

HRID 1634227Notes

Reaction equation

HRID 1634227 reaction equation
C(O[C:4](=O)[C:5]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH2:19])[C:11]=1[C:20]#[N:21])(C)[C:6](=O)[CH3:7])C.C(O)(=[O:25])C.OS(O)(=O)=O>O>[NH2:19][C:12]1[C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=[C:10]2[C:11]=1[C:20](=[O:25])[NH:21][C:6]([CH3:7])=[C:5]2[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 112667142-(3-Amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester

Product 1

HCID 235029378-amino-3,4-dimethyl-7-nitro-2H-isoquinolin-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

The ester from above (1.39 g, 4.56 mmol) was added to a mixture of acetic acid (20 mL), H2SO4 (3 mL) and water (2 mL), and the solution heated at 100° C. for 3 h. The cooled solution was diluted with water (30 mL), the precipitate was collected, washed with water and MeOH and dried to give 8-amino-3,4-dimethyl-7-nitro-2H-isoquinolin-1-one (0.76 g, 72%). mp>300° C.

Workup

  1. customthe precipitate was collected
  2. washwashed with water and MeOH
  3. customdried

Sources & evidence

ORD record
ord-19242b43304643afa29766e2f87f29b8
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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