1,2-Dimethoxyethane → O-Ethyl 3,7-dichloroquinoline-8-hydroxamate

HRID 2291449Notes

Reaction equation

HRID 2291449 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[C:13](Cl)=[O:14].C([N:18](CC)CC)C.[CH2:23]([CH2:26]OC)[O:24]C>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[C:13]([NH:18][O:24][CH2:23][CH3:26])=[O:14]

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 130908403,7-Dichloroquinolin-8-carbonyl Chloride

Product 1

HCID 15595572O-Ethyl 3,7-dichloroquinoline-8-hydroxamateYield 77%

Procedure

13.0 g (50 millimoles) of 3,7-dichloroquinoline-8-carbonyl chloride were suspended in 50 ml of dimethoxyethane, and 5.8 g (60 millimoles ) of 0-ethylhydroxyamine hydrochloride and 15 g (150 millimoles) of triethylamine were added. The mixture was stirred for 5 hours at room temperature, after which the solvent was removed in a rotary evaporator, the residue was triturated with water and the mixture was filtered under suction. 11.0 g (77%) of a product of melting point 140° C. were obtained (compound No. 21).

Workup

  1. customafter which the solvent was removed in a rotary evaporator
  2. customthe residue was triturated with water
  3. filtrationthe mixture was filtered under suction

Sources & evidence

ORD record
ord-0ee0aa717a654b2380859e82780de55b
Source dataset
uspto-grants-1989_01
Patent number
US04797148

Reaction notes

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