Triethylamine → ethyl N-(((5-nitro-8-quinolinyl)oxy)carbonyl)glycinate

HRID 2418224Notes

Reaction equation

HRID 2418224 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].[N:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]=[O:17].C(N(CC)CC)C>C(C(C)=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][C:16]([NH:15][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:17])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19910NitroxolineHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 13338831ethyl N-(((5-nitro-8-quinolinyl)oxy)carbonyl)glycinate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-Nitro-8hydroxyquinoline (19.0 g) was added to a solution containing 13.6 g of ethyl isocyanatoacetate in 250 ml of methyl ethyl ketone. This mixture was then stirred at room temperature while triethylamine (1.0 g) was added. Stirring was continued at ambient temperature for about 30 minutes when a crystalline mass precipitated. This crystalline solid was collected by filtration, washed with carbon tetrachloride and subsequently dried leaving the desired ethyl N-(((5-nitro-8-quinolinyl)oxy)carbonyl)glycinate as cream colored crystals, m.p. 121°-122° C.

Workup

  1. additionwas added
  2. customwhen a crystalline mass precipitated
  3. filtrationThis crystalline solid was collected by filtration
  4. washwashed with carbon tetrachloride
  5. customsubsequently dried

Sources & evidence

ORD record
ord-88dc274123964501b7b486a044d17e0c
Source dataset
uspto-grants-1984_09
Patent number
US04472404

Reaction notes

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