1,2-Dichloroethane → Quinoline

HRID 2259831Notes

Reaction equation

HRID 2259831 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.C(Cl)CCl>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 111,2-DichloroethaneHCID 7124Quinaldic AcidHCID 757711-Hydroxybenzotriazole

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 EDC (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% ethyl acetate) 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% ethyl acetate)

Sources & evidence

ORD record
ord-889dbd1fd6e2410d9cc1ad1aae94a4ab
Source dataset
uspto-grants-1995_12
Patent number
US05475013

Reaction notes

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