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

HRID 1378750노트

반응식

HRID 1378750 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 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.

후처리

  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 methanol/methylene chloride/hexane

출처 및 근거

ORD 기록
ord-bb8a91bd2299478f9e3837b9fee4c213
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668282

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