Dichloromethane → 2-(4-Chloro-[1,8]naphthyridin-2-yl)-benzonitrile

HRID 1404284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404284
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH2:16])=O)[CH:3]=1.ClCCl.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>>[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]#[N:16])[CH:3]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 673629212-(4-Chloro-[1,8]naphthyridin-2-yl)-benzamide

Produkt 1

HCID 673645562-(4-Chloro-[1,8]naphthyridin-2-yl)-benzonitrile

Versuchsvorschrift

To a slurry of 970 mg (3.42 mmol) 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzamide in 10 ml dichloromethane 2.85 g (12.0 mmol) 1.26 g (5.27 mmol) methoxycarbonylsulfamoyl-triethylammonium hydroxide, inner salt, (Burgess reagent) was added. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The residue was crystallized from isopropanol yielding 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzonitrile as colourless crystals; HPLC-MS: 1.94 min, [M+H] 266.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was crystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-9eee461fb7a04d74b2de1d8426b1f6f5
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912216B2

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