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

HRID 418510Notes

Reaction equation

HRID 418510 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 solvent was removed under reduced pressure and the residue purified by flash chromatography to afford the product as a yellow solid. MS m/z=269.4 (M+H). 1H NMR (400 MHz; CDCl3) 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. customthe solvent was removed under reduced pressure
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-0f267d5974de4a7abf1970aef920a4d0
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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