Ethyl Acetate → 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843882Notes

Reaction equation

HRID 1843882 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]1(=[O:16])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.C(OC(=O)C)C>OS(O)(=O)=O.CCCCCC>[N+:1]([C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][NH:7][C:6]2=[O:16])=[CH:11][CH:12]=1)([O-:4])=[O:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24434Potassium NitrateHCID 1508963,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-oneYield 61.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8058HexaneSolvent

Procedure

KNO3 (348 mg, 3.7414 mmol) was added to a solution of 3,4-dihydro-2H-isoquinolin-1-one (I-23b: 500 mg, 3.4013 mmol) in concentrated H2SO4 (10.2 mL) at 0° C. and the resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was quenched in chilled water and extracted with ethylacetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The concentrate was crystallized from diethyl ether to afford 400 mg of the product (61.2% yield).

Workup

  1. customThe reaction mixture was quenched in chilled water
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe concentrate was crystallized from diethyl ether

Sources & evidence

ORD record
ord-c5d3575e3d8b4f928ad81245e0da2c2a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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