Diisopropylethylamine → HCID 58230870, Verbindung

HRID 252237

Reaktionsgleichung

[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].CCN(C(C)C)C(C)C.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[OH:30]>C(Cl)Cl.C1COCC1.C(OCC)(=O)C>[OH:30][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:21]=1[NH:20][C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[C:25]([OH:27])=[O:26]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

2-methyl nicotinoyl chloride (0.2 g, 0.00128 mols) is dissolved in 30 ml dry DCM and N,N′-Diisopropylethylamine (0.994 g, 0.00769 mols) is added slowly to the acid chloride solution at 0° C. under nitrogen atmosphere. A solution of 4-Amino-3-hydroxybenzoic acid (0.196 g, 0.00128 mols) in 10 ml dry THF is slowly added to the above solution at 0° C. The solution is then stirred at 0° C. for 30 mins and then at RT overnight. The reaction mixture is then diluted with 100 ml Ethyl acetate and stirred for 30 mins. The precipitated tarry material is filtered off over celite bed and the organic phase given 4×20 ml water wash, 2×10 ml brine wash dried over sodium sulfate and rotary evaporated to get the crude amide (140 mg) which is taken for the cyclisation step without further purification.

Aufarbeitung

customat RT
customovernight
stirringstirred for 30 mins
filtrationThe precipitated tarry material is filtered off over celite bed
washwash
wash2×10 ml brine wash
dry with materialdried over sodium sulfate
customrotary evaporated

Quellen und Nachweise

ORD-Eintrag: ord-68113f6b2507438c962f16b003e8b0f2
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07868033B2

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