Quinaldic Acid → Quinoline

HRID 977152Notes

Reaction equation

HRID 977152 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][C:9](C(O)=O)=[N:10][C:4]2=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[N:10]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7124Quinaldic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 7047QuinolineYield 319.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A 100 ml RBF equipped with magnetic stir bar and N2 inlet was charged with 356 mg (2.06 mmol, 1 eq) 2-quinaldic acid in 10 ml dry DMF. The solution was cooled to 0° C. and 415 mg (3.07 mmol, 1.5 eq) HOBt was added followed by 415 mg EDCl (2.16 mmol, 1.05 eq). The reaction was stirred 2 hours at 0° C. when 1.1 g (2.06 mmol, 1 eq) of free asparagine amine in 10 ml dry DMF was added. The reaction was stirred at 0° C. for 2 hours then room temperature overnight. The reaction was poured into sat. bicarb and extracted with 2×65 mL ethyl acetate. The combined organics were washed with 5% aq. citric acid, brine, dried and concentrated to 1.4 g crude foam. Purification by flash chromatography on silica gel (100% EA) yielded 850 mg (61%) of quinoline adduct.

Workup

  1. customA 100 ml RBF equipped with magnetic stir bar and N2 inlet
  2. additionwas added
  3. customroom temperature overnight
  4. additionThe reaction was poured into sat. bicarb
  5. extractionextracted with 2×65 mL ethyl acetate
  6. washThe combined organics were washed with 5% aq. citric acid, brine
  7. customdried
  8. concentrationconcentrated to 1.4 g crude foam
  9. customPurification by flash chromatography on silica gel (100% EA)

Sources & evidence

ORD record
ord-c2759b3472434b9e96180212da15468d
Source dataset
uspto-grants-1997_03
Patent number
US05614522

Reaction notes

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