Triethylamine → HCID 14780582, compound

HRID 1650136Notes

Reaction equation

HRID 1650136 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:17]([CH2:18][OH:19])=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C(N(CC)CC)C>ClCCl.CS(C)=O>[Cl:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14780598HCID 14780598, compound

Product 1

HCID 14780582HCID 14780582, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (2.88 ml, 1.3 equivalents), in 25 ml of dichloromethane at -78° C. under nitrogen is added dropwise a solution of dimethylsulfoxide (DMSO) (4.70 ml, 2.6 equivalents) in 25 ml of dichloromethane. After addition, the mixture is stirred for 15 minutes at -78° C. and then a solution of 2-chloro-4-(4-fluorophenyl)-3-quinolinemethanol (7.30 g) in 50 ml dichloromethane and 20 ml dimethyl sulfoxide is added dropwise. The resulting mixture is stirred at -78° C. for one hour and then quenched by adding triethylamine (17.7 ml, 5.0 equivalents), and removing the cooling bath. A saturated aqueous solution of ammonium chloride is added. The organic layer is separated, washed with water, dried (magnesium sulfate), and evaporated to give 6.56 g of 2-chloro-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde as a yellow solid; mp 168°-169.5° C.; 1H NMR (chloroform-d): δ 10.25 (s, 1H), 8.12 (d, 1H), 7.91-7.83 (m, 1H), 7.57-7.53 (m, 2H), 7.36-7.22 (m, 4H) ppm.

Workup

  1. additionAfter addition
  2. stirringThe resulting mixture is stirred at -78° C. for one hour
  3. customquenched
  4. customremoving the cooling bath
  5. additionA saturated aqueous solution of ammonium chloride is added
  6. customThe organic layer is separated
  7. washwashed with water
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated

Sources & evidence

ORD record
ord-3efd297be801438fb43fa94975aa7e10
Source dataset
uspto-grants-1990_05
Patent number
US04923861

Reaction notes

Loading…