Ethanolamine → 6-Chloro-2-(2-hydroxyethyl)-5-nitroisoquinolin-1(2H)-one

HRID 1161293Notes

Reaction equation

HRID 1161293 reaction equation
[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[CH:5]2.[CH2:16]([CH2:18][NH2:19])[OH:17].C(N(CC)CC)C.CO>>[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:19]([CH2:18][CH2:16][OH:17])[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 700EthanolamineHCID 887MethanolHCID 8471TriethylamineHCID 595157256-Chloro-5-nitro-1H-isochromen-1-one

Product 1

HCID 595156676-Chloro-2-(2-hydroxyethyl)-5-nitroisoquinolin-1(2H)-one

Procedure

A microwave vial was charged with 6-chloro-5-nitro-1H-isochromen-1-one (1.0 g, 0.00443 mol), ethanolamine (0.401 mL, 0.00665 mol), triethylamine (1.24 mL, 0.00886 mol) and methanol (30 mL, 0.7 mol) and the reaction was subjected to microwave at 100° C. for 1 hour. The reaction was complete in the sense that all the starting material was consumed but the major product formed was the chloro displacement with the amine. The solvent was removed and the residue purified by flash chromatography to obtain the product as a yellow solid. MS m/z=269.4 (M+H). 1H NMR (400 MHz; CDCl3) δ 8.41 (d, J=8.56 Hz, 1H), 7.52 (d, J=8.56 Hz, 1H), 7.33 (d, J=8.4 Hz, 1H), 6.31 (d, J=8.56 Hz, 1H), 4.17 (t, J=44.88 Hz, 2H), 3.99 (t, J=5.11 Hz, 2H), 2.55 (bs, 1H).

Workup

  1. customwas consumed
  2. customthe major product formed
  3. customThe solvent was removed
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-05ad252e3cbf405aa74f247c074055eb
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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