Ammonium Chloride → 2-(3-Benzo[b]furyl)-6,7-methylenedioxyquinolin-4-one

HRID 38652

Reaktionsgleichung

Reaktionsgleichung von HRID 38652
[C:1]([C:4]1[C:5]([NH:13][C:14]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][CH:17]=2)=O)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+].[Cl-].[NH4+].[K+].[Br-]>C(O)(C)(C)C>[O:18]1[CH:17]=[C:16]([C:14]2[CH2:2][C:1](=[O:3])[C:4]3[C:5](=[CH:6][C:7]4[O:11][CH2:10][O:9][C:8]=4[CH:12]=3)[N:13]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]1=2

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 253877Potassium BromideHCID 23665647Potassium tert-butoxideHCID 44220313N-(6-acetyl-1,3-benzodioxol-5-yl)-1-benzofuran-3-carboxamide

Produkt 1

HCID 666593752-(3-Benzo[b]furyl)-6,7-methylenedioxyquinolin-4-oneAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Into a suspension of 155 (2.95 mmol) in t-butyl alcohol (100 mL) was added potassium t-butoxide (1.66 g, 14.7 mmol). The mixture was refluxed under argon for 12 h, cooled, and poured into a 10% ammonium chloride solution (100 mL). The solid precipitate was collected and washed with EtOH. The crude product was purified by flash chromatography (silica gel, CH2Cl2: EtOH 16:1-10:1). Obtained as a pale-yellow solid from 155; yield 17%; mp>315° C.; ESI-MS (Positive mode): m/z 306 [M+H]+; 1H-NMR (400 MHz, DMSO-d6): δ 6.12 (2H, s), 6.49 (1H, s), 7.13 (1H, s), 7.36-7.45 (3H, m), 7.69 (1H, d, J=8.0 Hz), 8.14 (1H, s), 8.52 (1H, s); IR (KBr): 1626 (C═O) cm−1; Anal. Calcd for C18H11NO4: C, 70.82; H, 3.63; N, 4.59. Found: C, 70.52; H, 3.95; N, 4.21.

Aufarbeitung

  1. temperatureThe mixture was refluxed under argon for 12 h
  2. temperaturecooled
  3. customThe solid precipitate was collected
  4. washwashed with EtOH
  5. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2: EtOH 16:1-10:1)
  6. customObtained as a pale-yellow solid from 155

Quellen und Nachweise

ORD-Eintrag
ord-ea4eb7671aec40e3af57090807affc90
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

Verknüpfte Notizen

Wird geladen…