5-Chloro-8-hydroxyquinoline → HCID 13338832, compound

HRID 2418225Notes

Reaction equation

HRID 2418225 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18].C(N(CC)CC)C>C(C(C)=O)C>[Cl:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2

Participants

5

Reactant 3

HCID 28175-Chloro-8-hydroxyquinolineHCID 8471TriethylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 13338832HCID 13338832, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-Chloro-8-hydroxyquinoline (35.9 g), 2-chloroethyl isocyanate (21.1 g), and triethylamine (2.02 g) were mixed in 400 ml of methyl ethyl ketone and heted at reflux temperature with stirring for about one hour. The reaction mixture, upon cooling to room temperature, yielded the desired 5-chloro-8-quinolinyl N-(2chloroethyl)carbamate as glistening, cream colored cystals, m.p. 146° C.

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-7bbe69641fd54f4bb7b06d37cb63f803
Source dataset
uspto-grants-1984_09
Patent number
US04472404

Reaction notes

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