Acetyl chloride → 4-Acetyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 1736692Notes

Reaction equation

HRID 1736692 reaction equation
C(Cl)(=O)C.[C:5]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15](=[O:23])[CH2:14]1)(=[O:12])[C:6]1C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[C:5]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15](=[O:23])[CH2:14]1)(=[O:12])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 7343784-Benzoyl-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 27708254-Acetyl-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.36 ml) is added to 1,2,3,4-tetrahydroquinoxalin-2-one (IV, EXAMPLE 1, 0.676 g) and triethylamine (0.76 ml) in THF (8 ml) at 0°. After stirring for 1 hr, the solvent is removed under reduced pressure and the residue is partitioned between dichloro-methane and aq. sodium bicarbonate. The layers are separated, the organic phase is filtered through sodium sulfate and concentrated. The concentrate is crystallized from methanol/methylene chloride/hexane to give the title compound, mp 164°-165°; NMR (CDCl3) 2.28, 4.54, 7.00, 7.11, 7.21 and 9.19 δ.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customthe residue is partitioned between dichloro-methane and aq. sodium bicarbonate
  3. customThe layers are separated
  4. filtrationthe organic phase is filtered through sodium sulfate
  5. concentrationconcentrated
  6. customThe concentrate is crystallized from methanol/methylene chloride/hexane

Sources & evidence

ORD record
ord-f518f3b0d48c41d7aed560e5f6a6e213
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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