Chloroxine → HCID 13338830, compound

HRID 2418223Notes

Reaction equation

HRID 2418223 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:15]=[O:16].C(N(CC)CC)C>C(C(C)=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13][C:15]([NH:14][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 2722ChloroxineHCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 13338830HCID 13338830, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5,7-Dichloro-8-hydroxyquinoline (21.4 g), ethyl isocyanatoacetate (21.3 g) and triethylamine (1.0 ml) were mixed together in 400 ml of methyl ethyl ketone and stirred at room temperature for about 42 hours resulting in the precipitation of a white crystalline solid. This solid was removed from the reaction mixture by filtration and was determined to be the desired ethyl N-(((5,7-dichloro-8-quinolinyl)oxy)carbonyl)glycinate, m.p. 119.5° C.

Workup

  1. customresulting in the precipitation of a white crystalline solid
  2. customThis solid was removed from the reaction mixture by filtration

Sources & evidence

ORD record
ord-4c22a42936bb411cabc8e3b68320b141
Source dataset
uspto-grants-1984_09
Patent number
US04472404

Reaction notes

Loading…