Methanol → 2-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-5-nitro-2H-isoquinolin-1-one

HRID 1624983Notes

Reaction equation

HRID 1624983 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].[O:15]1[C:20]2[CH:21]=[CH:22][C:23]([CH2:25][NH2:26])=[CH:24][C:19]=2[O:18][CH2:17][CH2:16]1.CO>>[O:15]1[C:20]2[CH:21]=[CH:22][C:23]([CH2:25][N:26]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[CH:13][C:4]=4[N+:1]([O-:3])=[O:2])[C:9]3=[O:14])=[CH:24][C:19]=2[O:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 887MethanolHCID 871022,3-Dihydro-1,4-benzodioxin-6-methylamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 582704062-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-5-nitro-2H-isoquinolin-1-one

Procedure

5-Nitro-isochromen-1-one (1.0 g, 0.0052 mol) and C-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-methylamine (1.0 g, 0.0060 mol) were refluxed in methanol (40 mL, 1 mol) for 2 hours. The solvent was removed and the residue was purified via flash chromatography (40 g of silica gel, 0-30% EtOAc/Hexanes) gave a yellow solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified via flash chromatography (40 g of silica gel, 0-30% EtOAc/Hexanes)
  3. customgave a yellow solid

Sources & evidence

ORD record
ord-af9602cbcd30498d9d32c0330c00daef
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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