Hydrochloric Acid → Ethyl 6-chloro-4-(2-fluoro-4-methylanilino)nicotinate

HRID 917743

Reaktionsgleichung

Reaktionsgleichung von HRID 917743
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([Cl:22])[CH:12]=1.Cl>CCO>[Cl:22][C:13]1[CH:12]=[C:11]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=2[F:1])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 679842-Fluoro-4-methylanilineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Produkt 1

HCID 23630706Ethyl 6-chloro-4-(2-fluoro-4-methylanilino)nicotinateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Fluoro-4-methylaniline and ethyl 4,6-dichloronicotinate were reacted in a mixture of EtOH and conc. HCl as for example 33, step A. The resultant solid was isolated by filtration and washed with 10% Et2O/Hexane, to give ethyl 6-chloro-4-(2-fluoro-4-methylanilino)nicotinate (44%); m.p. (EtOH/water) 107-109° C. 1H NMR [400 MHz, CDCl3] δ 9.63 (br s, 1H), 8.77 (s, 1H), 7.20 (t, J=8.2 Hz, 1H), 7.05-6.99 (m, 2H), 6.65 (d, J=1.6 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H). MS (FAB+) 309 (40%).

Aufarbeitung

  1. customThe resultant solid was isolated by filtration
  2. washwashed with 10% Et2O/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-b6c4aa72cff54fcd8690395d0accb8fa
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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