Oxalyl chloride → HCID 135819170, compound

HRID 1748371Notes

Reaction equation

HRID 1748371 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-4039806253cd4b759232b821f5a64424
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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