Methanol → 2-(1,3-Dihydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

HRID 1161190Notes

Reaction equation

HRID 1161190 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].[NH2:15][CH:16]([CH2:19][OH:20])[CH2:17][OH:18].CO.C(N(CC)CC)C>>[OH:18][CH2:17][CH:16]([N:15]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])[CH2:19][OH:20]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 68294SerinolHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 595157632-(1,3-Dihydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

Procedure

5-nitro-isochromen-1-one (4.2 g, 0.022 mol) and Serinol (2.0 g, 0.022 mol) were refluxed in methanol (40 mL, 1 mol) for 1 hour. TLC showed that all of the starting material was consumed. Triethylamine (5 mL, 0.04 mol) was added to the mixture and the reaction mixture was refluxed overnight. The volatiles were removed via rotovapor, and the residue was purified by flash column chromatography (40 g of silica gel, 0-50% EtOAc/Hexane), and gave a green yellow solid. MS m/z=264.7 (M+1).

Workup

  1. customwas consumed
  2. temperaturethe reaction mixture was refluxed overnight
  3. customThe volatiles were removed via rotovapor
  4. customthe residue was purified by flash column chromatography (40 g of silica gel, 0-50% EtOAc/Hexane)
  5. customgave a green yellow solid

Sources & evidence

ORD record
ord-8fce3679bd0f48d0b0e6fbad1ebd2f0e
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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