Pyridine → 2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

HRID 1161294Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][OH:15])[CH:6]=[CH:5]2.[C:19](OC(=O)C)(=[O:21])[CH3:20].N1C=CC=CC=1.C(Cl)Cl>>[C:19]([O:15][CH2:14][CH2:13][N:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=2[N+:16]([O-:18])=[O:17])[C:8]1=[O:12])(=[O:21])[CH3:20]

Participants

Reactant 4

HCID 1049Pyridine

HCID 6344Dichloromethane

HCID 7918Acetic Anhydride

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

Product 1

HCID 595159062-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Procedure

A round bottom flask was charged with 6-chloro-2-(2-hydroxyethyl)-5-nitroisoquinolin-1(2H)-one (400.0 mg, 0.00149 mol), acetic anhydride (0.21 mL, 0.0022 mol), pyridine (0.18 mL, 0.0022 mol) and methylene chloride (20 mL, 0.2 mol) and the reaction stirred at room temperature over night. The solvent was removed to obtain the product as a yellow solid. MS m/z=311.3 (M+H).

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-0b310bc247884c7a889b07c16a31da32
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816371B2

Reaction notes

Loading…