Tetrahydrofuran → 4-(furan-2-carbonyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 1378751Notes

Reaction equation

HRID 1378751 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].C([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19](=[O:27])[CH2:18]1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.C1COCC1>C(=O)(O)[O-].[Na+]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19](=[O:27])[CH2:18]1)=[O:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 7343784-Benzoyl-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 27870894-(furan-2-carbonyl)-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

2-Furoyl chloride (0.49 ml) is added to a solution of the 1,2,3,4-tetrahydroquinoxalin-2-one (IV, EXAMPLE 1, 710 mg), triethylamine (0.80 ml), and THF (20.0 ml) at 0°. The mixture is stirred for 1.5 hr at 0° and for 2 hr at 20°-25°. The mixture was diluted with aq. sodium bicarbonate and extracted with ethyl acetate and chloroform several times. The organic phases are combined, dried with magnesium sulfate, concentrated, and recrystallized from hot ethyl acetate to give the title compound, mp 229°-230° ; IR (mineral oil) 2954, 2925, 1684, 1648, 1504, 1474, 1391, 1373 and 756 cm-1 ; NMR (CDCl3) 8.53, 7.39, 7.1-7.25, 6.85-7.05, 6.45 and 4.59 δ; MS (m/z) 242 and 95.

Workup

  1. extractionextracted with ethyl acetate and chloroform several times
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customrecrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-e2a598214d894bbabfc1107ee936369b
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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