Water → Ethyl 4-azido-7-chloroquinoline-3-carboxylate

HRID 1862820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862820
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1Cl)=[CH:17][CH:16]=[C:15]([Cl:21])[CH:14]=2)=[O:9])[CH3:6].O>CN(C)C=O>[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[N:1]=[N+:2]=[N-:3])=[CH:17][CH:16]=[C:15]([Cl:21])[CH:14]=2)=[O:9])[CH3:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 12256460Ethyl 4,7-dichloroquinoline-3-carboxylate

Produkt 1

HCID 3690236Ethyl 4-azido-7-chloroquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium azide (0.62 g; 0.009 M) was suspended in a solution of ethyl-4,7-dichloroquinoline-3-carboxylate E. F. Elslager, et al., J. Med. Pharm, Chem, 5, 550 (1962) (1.75 g; 0.006 M) in dry dimethyl formamide (20 ml) and this mixture stirred at ambient temperatures. After 18 hr. the mixture was poured into reapidly stirred water (200 ml), the resultant precipitate filtered off, dried at the pump and then recrystallised from ethanol (8 ml/g), 1.27 g (71%), m.p. 94.5° C., (Found: C, 51.7; H, 3.4; N, 20.2; Cl, 12.9% C12H9N4O2Cl requires C, 52.0; H, 3.3; N, 20.2; Cl, 12.8%); max (KBr) 2140, 1722, 1390, 1372, 1274, 1239, 1199 and 1058 cm-1, (CDCl3) 1.48 (t) and 4.55 (m) (CH3CH2), 7.59 (m), 8.11 (d), 8.32 (d) and 9.29 (s) (aromatic H's) m/e 276 (M+, 14%), 248 (9%), 218 (22%), 154 (29% 152 (100%).

Aufarbeitung

  1. filtrationthe resultant precipitate filtered off
  2. customdried at the pump
  3. customrecrystallised from ethanol (8 ml/g), 1.27 g (71%), m.p. 94.5° C., (Found: C, 51.7; H, 3.4; N, 20.2; Cl, 12.9% C12H9N4O2Cl requires C, 52.0; H, 3.3; N, 20.2; Cl, 12.8%)

Quellen und Nachweise

ORD-Eintrag
ord-2f02153f3559465c89cf9b203bd50cc8
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04166817

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