Hydrochloric Acid → HCID 123771552, Verbindung

HRID 1470526Notizen

Reaktionsgleichung

[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].[C:16]1([NH:22][C:23]2[N:30]=[CH:29][CH:28]=[CH:27][C:24]=2[CH:25]=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CO>[C:16]1([NH:22][C:23]2[C:24]([CH:25]=[CH:1][C:2]([C:4]3[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:12][CH3:13])=[C:8]([O:10][CH3:11])[CH:9]=3)=[O:3])=[CH:27][CH:28]=[CH:29][N:30]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 30 °C

Versuchsvorschrift

To a stirred solution of 3,4,5-trimethoxyacetophenone (213 mg, 1.01 mmol) in methanol (5 mL) was added 2N Ba(OH)2 solution (2 mL) after 5 minutes to the reaction mixture 2-(phenylamino)nicotinaldehyde (200 mg, 1.01 mmol) was added, stirred for 6 h at 30° C. The progress of the reaction was monitored by TLC for completion. After completion of the reaction, the reaction mixture was acidified with 2N HCl, the resulting precipitate was filtered, washed thoroughly with water and dried over anhydrous CaCl2. The resulting product was purified by by recrystallization from ethanol to afford compound 6a as a pale yellow solid (365 mg, 92% yield).; mp 125-128° C. 1H NMR (CDCl3): δ 8.26 (d, 1H, J=4.1 Hz), 8.01 (d, 2H, J=8.3 Hz), 7.95 (d, 1H, J=15.8 Hz), 7.81 (d, 1H, J=8.3 Hz), 7.55 (d, 1H, J=16.1 Hz), 7.48 (q, 2H), 7.01-7.09 (m, 3H), 6.83 (q, 1H), 6.62 (s, 1H), 3.91 (s, 3H) 3.84 (s, 6H); ESI MS: 391 (M+1)+.

Aufarbeitung

additionwas added
customAfter completion of the reaction
filtrationthe resulting precipitate was filtered
washwashed thoroughly with water
dry with materialdried over anhydrous CaCl2
customThe resulting product was purified by by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-de5790abaf1441fdb0b0a6433e1ee128
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09006451B1

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