Benzylamine → 2-benzyl-5-nitroisoquinolin-1(2H)-one

HRID 459835Notes

Reaction equation

HRID 459835 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)C>[CH2:15]([N:22]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 184445282-benzyl-5-nitroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

5-Nitro-isochromen-1-one (1.0 g, 5.23 mmol) from step 2 was dissolved in excess benzylamine (5 mL) and heated to 80° C. for 4 hours. The mixture was then diluted in diethyl ether and washed several times with (0.5 N) HCl. The organic layer was concentrated in vacuo to give 2-benzyl-5-nitro-2H-isoquinolin-1-one as a yellow solid.

Workup

  1. washwashed several times with (0.5 N) HCl
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0b81584965e346eb81978a93de1024db
Source dataset
uspto-grants-2007_03
Patent number
US07196088B2

Reaction notes

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