Methanol → 5-Nitro-2-(pyridin-2-ylmethyl)-1,2-dihydroisoquinolin-1-one

HRID 1037780Notes

Reaction equation

HRID 1037780 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].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][NH2:22].CO>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:22]([CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=1)[C:9]2=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 195092-PyridinemethanamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 595795135-Nitro-2-(pyridin-2-ylmethyl)-1,2-dihydroisoquinolin-1-oneYield 49.8%

Conditions

Temperature
150 °C

Procedure

Into a microwave vial was combined 5-nitro-isochromen-1-one (1 g, 0.005 mol), 2-pyridinemethanamine (1 g, 0.009 mol), and methanol (20 mL, 0.5 mol). The mixture was heated at 150° C. for 2 hours. The mixture was cooled to room temperature. The usual work up of the reaction mixture gave a crude product which was then purified using a flash chromatography over silica gel to give the pure product as a yellow solid (0.7 g). MS m/z=282.4 (M+1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe usual work up of the reaction mixture gave a crude product which
  3. customwas then purified

Sources & evidence

ORD record
ord-b02891cdcccb47a2942b6a49bc62fd04
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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