Broxyquinoline → HCID 13338828, compound

HRID 2418221Notes

Reaction equation

HRID 2418221 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([Br: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>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]([Br: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 2453BroxyquinolineHCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 13338828HCID 13338828, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,7-Dibromo-8-hydroxyquinoline (19.7 g), ethyl isocyanatoacetate (13.0 g) and triethylamine (6.58 g) were mixed in 200 ml of toluene and heated at reflux temperature for about 47 hours. The solution was cooled to room temperature and the desired ethyl N-(((5,7-dibromo-8-quinolinyl)oxy)carbonyl)glycinate was obtained as a white, crystalline solid, m.p. 129.5° C. (decomposition).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for about 47 hours

Sources & evidence

ORD record
ord-352584ebf65840878a856e4511bd0af2
Source dataset
uspto-grants-1984_09
Patent number
US04472404

Reaction notes

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