Oxalyl chloride → HCID 135819170, compound

HRID 513921Notes

Reaction equation

HRID 513921 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12]C)=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].OC1C2C(=CC(OC)=CC=2)N=CC=1C(OCC)=O.C(Cl)(=O)C(Cl)=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CN(C=O)C>[OH:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 728976Ethyl 4-chloro-7-methoxyquinoline-3-carboxylateHCID 178469633HCID 178469633, compound

Product 1

HCID 135819170HCID 135819170, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate. To a solution of ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate (2.72 g, 11.0 mmol) in chloroform (100 mL) was added oxalyl chloride (2.93 mL, 33.0 mmol) followed by 5 drops of DMF. The reaction was heated at 65° C. for 2.5 h before cooling to ambient temperature. The reaction mixture was poured into saturated NaHCO3 (aq.) solution and the organics were extracted with DCM. The combined organics were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound as a yellow solid (2.69 g, 92%). 1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1H), 8.33 (d, J=9.4 Hz, 1H), 7.58 (br. s., 1H), 7.37 (d, J=9.0 Hz, 1H), 4.48 (q, J=6.8 Hz, 2H), 4.01 (s, 3H), 1.45 (t, J=7.0 Hz, 3H). [M+H]=266.2.

Workup

  1. temperaturebefore cooling to ambient temperature
  2. extractionthe organics were extracted with DCM
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cda2ca7dc7a0470b956aae1f4118956e
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

Loading…