Dimethyl Sulfoxide → HCID 14780586, compound

HRID 1650140Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][N:12]([CH3:34])[C:13]1[C:22](/[CH:23]=[CH:24]/[CH2:25][OH:26])=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH3:34][N:12]([CH3:11])[C:13]1[C:22](/[CH:23]=[CH:24]/[CH:25]=[O:26])=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl chloride (1.21 ml, 1.3 equivalents), in 40 ml of dichloromethane at -78° C. under an atmosphere of nitrogen, is added a solution of 2.0 ml (2.6 equivalents) of dimethylsulfoxide in 25 ml of dichloromethane. The reaction is stirred at -78° C. for 15 minutes and 3.45 g of (E)-3-[2-(dimethylamino)-4-(4-fluorophenyl)-3-quinolinyl]-2-propen-1-ol in 40 ml of dichloromethane added dropwise. The reaction is stirred for one hour at -78° C. and then quenched by adding 7.46 ml (5.0 equivalents) of triethylamine and warming to room temperature. A saturated aqueous solution of ammonium chloride, 20 ml, is added and the reaction is washed with water, dried (magnesium sulfate), and evaporated to give 3.14 g of (E)-3-[2-(dimethylamino)-4-(4-fluorophenyl)-3-quinolinyl]-2-propenal as an orange solid; 1H NMR (chloroform-d): δ 9.35 (d, 1H), 7.75 (d, 1H), 7.58-6.98 (m, 8H), 6.32 (dd, 1H), 2.99 (s, 6H) ppm.

Workup

stirringThe reaction is stirred for one hour at -78° C.
customquenched
temperaturewarming to room temperature
washthe reaction is washed with water
dry with materialdried (magnesium sulfate)
customevaporated

Sources & evidence

ORD record: ord-c15ff323048549a8bc2b073694d25cbe
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923861

Reaction notes

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