Triethylamine → HCID 19754488, compound

HRID 1588730Notes

Reaction equation

HRID 1588730 reaction equation
[C:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8](C(O)=O)=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C>C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([O:16][CH3:17])=[CH:7][C:8]([N:37]=[C:40]=[O:25])=[CH:12][C:13]=1[O:14][CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 225680Acetyl syringic acid

Product 1

HCID 19754488HCID 19754488, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of 4-acetoxy-3,5-dimethoxybenzoic acid (672 mg), diphenylphosphoryl azide (990 mg) and benzene (15 ml) was dropwise added triethylamine (0.42 ml), while stirring. The mixture was stirred for 20 minutes at room temperature and further for 30 minutes under refluxing to obtain a solution of 4-acetoxy-3,5-dimethoxyphenyl isocyanate in benzene. 3-Amino-4-(2-chlorophenyl)-1,6,7-trimethyl-2(1H)-quinolone (624 mg) was added to the above solution and the mixture was refluxed for 2.5 hours. The mixture was washed with water, aqueous sodium hydrogen carbonate solution, water, diluted hydrochloric acid and then water in this order, dried (MgSO4) and concentrated.

Workup

  1. stirringThe mixture was stirred for 20 minutes at room temperature and further for 30 minutes
  2. temperatureunder refluxing

Sources & evidence

ORD record
ord-88728f76a2ce4144b0564cba922eebea
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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