Triethylamine → HCID 11725089, compound

HRID 865024Notes

Reaction equation

HRID 865024 reaction equation
C([N:3]([CH2:6]C)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14](=[O:20])[C:13](C(O)=O)=[C:12]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>C1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14](=[O:20])[C:13]([N:3]=[C:6]=[O:38])=[C:12]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10427811HCID 10427811, compound

Product 1

HCID 11725089HCID 11725089, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Triethylamine (0.7 ml, 5 mmol) was added dropwise with stirring at room temperature to a solution of 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-1-methyl-2-oxoquinoline-3-carboxylic acid (1.75 g, 5 mmol) and diphenylphosphoryl azide (1.19 ml, 5.5 mmol) in 35 ml benzene. The mixture was stirred at room temperature for 15 minutes and then refluxed for 30 minutes to yield a solution of 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-3-isocyanato-1-methyl-2-oxoquinoline. 4-Nitrobenzyl alcohol (2.31 g, 15.1mmol) and dibutyltin oxide (35 mg) were added to the cooled reaction mixture which was then refluxed for 4 h. The reaction solution was cooled to room temperature, washed with water, dried (sodium sulfate) and concentrated in vacuo. The solid residue was purified by column chromatography on silica gel (650 g), eluting with 3:2 hexane/ethyl acetate to yield the title compound as an off-white solid (1.9 g, 76% yield).

Workup

  1. temperaturerefluxed for 30 minutes

Sources & evidence

ORD record
ord-932d6ff253334929bf44a57cc6215a8b
Source dataset
uspto-grants-1996_10
Patent number
US05565472

Reaction notes

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