Quinaldic Acid → 2-Quinolinecarbonyl azide

HRID 1456296Notes

Reaction equation

HRID 1456296 reaction equation
C(N(CC)CC)C.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([OH:20])=O.C1(P([N:35]=[N+:36]=[N-:37])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([N:35]=[N+:36]=[N-:37])=[O:20]

Participants

5

Reactant 3

HCID 7124Quinaldic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 116297802-Quinolinecarbonyl azideYield 263.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

47 ml (0.34 mol) of triethylamine are added to a stirred suspension, cooled to -10° C., of 30.0 g (0.17 mol) of quinoline-2-carboxylic acid in 385 ml of anhydrous tetrahydrofuran, and the mixture is stirred at -10° C. for 10 minutes, whereupon a clear solution forms. 73.0 ml (0.34 mol) of diphenylphosphoryl azide are then added dropwise and the reaction mixture is left to stand in a refrigerator at 0° C. for 20 hours. Thereafter, the mixture is stirred into 350 ml of ice-cold dilute NaHCO3 solution. The precipitate formed is separated off by filtration, washed with water and dried in air. 88.9 g (86%) of the title compound are obtained as a pale solid.

Workup

  1. waitthe reaction mixture is left
  2. waitto stand in a refrigerator at 0° C. for 20 hours
  3. customThe precipitate formed
  4. customis separated off by filtration
  5. washwashed with water
  6. customdried in air

Sources & evidence

ORD record
ord-394e6c9b227e4a05a68b6dd1445a083c
Source dataset
uspto-grants-1998_12
Patent number
US05843967

Reaction notes

Loading…