Dimethyl Sulfoxide → 4-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)butanal

HRID 1846991Notes

Reaction equation

HRID 1846991 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][C:17]1=[O:28].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH3:27][O:26][C:23]1[CH:24]=[C:25]2[C:20]([N:19]=[CH:18][C:17](=[O:28])[N:16]2[CH2:15][CH2:14][CH2:13][CH:12]=[O:11])=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 867249221-(4-Hydroxybutyl)-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249234-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)butanalYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of oxalyl chloride (0.171 ml, 1.99 mmol) in dichloromethane (5 ml) was cooled to −78° C., a solution of dimethyl sulfoxide (0.283 ml, 3.99 mmol) in dichloromethane (5 ml) was added dropwise under a stream of argon and the reaction mixture was stirred at the same temperature for 15 minutes. A solution of 1-(4-hydroxybutyl)-7-methoxyquinoxalin-2(1H)-one (198 mg, 0.797 mmol) in dichloromethane (5 ml) was added dropwise and the reaction mixture was further stirred at the same temperature for 1 hour. Triethylamine (0.833 ml, 5.98 mmol) was added thereto, the temperature was raised to room temperature and a saturated ammonium chloride aqueous solution and dichloromethane were added. After stirring, the organic layer was separated, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 114 mg (58%) of the title compound in the form of a yellow solid.

Workup

  1. stirringthe reaction mixture was further stirred at the same temperature for 1 hour
  2. stirringAfter stirring
  3. customthe organic layer was separated
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4cc37a7fee2b4affaa39d394e70c02c4
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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