Benzoyl chloride → 4-Benzoyl-1,2,3,4-tetrahydroquinoxalin-2-one

HRID 1899935Notes

Reaction equation

HRID 1899935 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6](C)(C)[NH:5]2.C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:22]([N:5]1[C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[NH:8][C:7](=[O:12])[CH2:6]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 229128926-Fluoro-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 7343784-Benzoyl-1,2,3,4-tetrahydroquinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2,3,4-tetrahydroquinoxalin-2-one (IV, EXAMPLE 1, 0.593 g) and triethylamine (0.725 ml) in THF (5 ml) is cooled at 0°. To this is added benzoyl chloride (0.56 ml). After the addition is complete, the ice bath is removed and additional THF (5 ml) is added. The reaction is stirred for 30 min and then partitioned between ethyl acetate, aq. sodium bicarbonate, and saline. The organic phases are separated and the organic phase is dried over magnesium sulfate and concentrated. The crude product is recrystallized from methanol/dichloromethane/hexane to give the title compound, mp 208.0°-208.5°; MS (m/z) at 252; IR (mineral oil) 1684, 1666, 1502, 757 and 1362 cm-1 ; NMR (CDCl3) 4.58, 6.7, 6.79, 6.98, 7.10, 7.34 and 7.40 δ.

Workup

  1. temperatureis cooled at 0°
  2. additionAfter the addition
  3. customthe ice bath is removed
  4. additionadditional THF (5 ml) is added
  5. custompartitioned between ethyl acetate, aq. sodium bicarbonate, and saline
  6. customThe organic phases are separated
  7. dry with materialthe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product is recrystallized from methanol/dichloromethane/hexane

Sources & evidence

ORD record
ord-6811553f3b2e465fb76862e594a8bab6
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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