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

HRID 1899936Notes

Reaction equation

HRID 1899936 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].F[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[C:10](C)(C)[NH:9]2.C(N(CC)CC)C>C1COCC1>[C:1]([N:9]1[C:8]2[C:13](=[CH:14][CH:15]=[CH:6][CH:7]=2)[NH:12][C:11](=[O:16])[CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 229128926-Fluoro-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-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 dichloromethane and aq. sodium bicarbonate. The layers are separated, the organic phase is filtered through sodium sulfate and concentrated. The concentrate is crystallized from methanomethylene 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 dichloromethane 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 methanomethylene chloride/hexane

Sources & evidence

ORD record
ord-f0b3fe839b9c4397ad759c08e9436e5e
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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