2,5-Dimethoxytetrahydrofuran → 6-(1H-Pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione

HRID 2236409Notes

Reaction equation

HRID 2236409 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]2.CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1.Cl.ClC1C=CN=CC=1>O1CCOCC1>[N:1]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]3)[CH:16]=[CH:20][CH:19]=[CH:18]1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 818524-Chloropyridine hydrochlorideHCID 116224226-Aminoisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 593003906-(1H-Pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dioneYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-amino-4H-isoquinoline-1,3-dione (1 g, 5.68 mmol), 2,5-dimethoxytetrahydrofuran (0.736 mL, 5.68 mmol), 4-chloropyridine hydrochloride (0.417 g, 2.78 mmol) in dioxane (20 mL) is heated at 70° C. for 2 h [Ref: J. Heterocyclic Chem. 35, 1313, (1998)] After cooling, the solid is filtered, washed successively with water, ether and hexane to yield 0.86 g (67%) of the title compound as a light brown solid, mp 212-213° C.; HRMS (ESI) m/z calcd for C13H10N2O2 227.08151. found 227.08151 (M+H)+1. Analysis for C13H10N2O2 (0.5H2O): Calcd: C, 66.37; H, 4.71; N, 11.91. Found: C, 66.19; H, 4.56; N, 11.09.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered
  3. washwashed successively with water, ether and hexane

Sources & evidence

ORD record
ord-36da003173064ea4a7a1a42336a8fd0e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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