Dimethyl Sulfoxide → HCID 19029397, compound

HRID 2256312Notes

Reaction equation

HRID 2256312 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:33][CH2:34][OH:35])[CH2:20][C:21]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25][CH2:24]2)=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].CCN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:33][CH:34]=[O:35])[CH2:20][C:21]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25][CH2:24]2)=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 190293711-[3-(3,4-Dichlorophenyl)-5-hydroxy-1-oxopentyl]-1,2,3,4-tetrahydroquinoline

Product 1

HCID 19029397HCID 19029397, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (1.15 mL) in CH2Cl2 (30 mL) was cooled to -78° C. whereupon DMSO (1.87 mL) was added dropwise over 15 mins. This mixture was stirred for 15 minutes. Whereupon a CH2Cl2 (30 mL) solution of 1-[3-(3,4-dichlorophenyl)-5-hydroxy-1-oxopentyl]-1,2,3,4-tetrahydroquinoline (1.0 g) was added over 20 minutes. The mixture was stirred for 30 minutes and then treated with Et3N (7.4 mL) and stirred for an additional 30 minutes at -78° C., followed by 1.5 hours at room temperature. The reaction mixture was quenched with water and diluted with CH2Cl2 (100 mL). The organic fraction was separated, washed sequentially with 1N HCl (1×50 mL), sat. NaHCO3 (1×50 mL) and brine (1×50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to yield an oil. Silica gel chromatography eluting with 5-15% EtOAc/Hex gave the title compound (900 mg).

Workup

  1. additionwas added dropwise over 15 mins
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringstirred for an additional 30 minutes at -78° C.
  4. waitfollowed by 1.5 hours at room temperature
  5. customThe reaction mixture was quenched with water
  6. additiondiluted with CH2Cl2 (100 mL)
  7. customThe organic fraction was separated
  8. washwashed sequentially with 1N HCl (1×50 mL), sat. NaHCO3 (1×50 mL) and brine (1×50 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto yield an oil
  13. washSilica gel chromatography eluting with 5-15% EtOAc/Hex

Sources & evidence

ORD record
ord-3263d9bb00a54e4683212eb0ee875d3c
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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