Hydrochloric Acid → Ethyl 6-chloro-4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]nicotinate

HRID 917756

Reaktionsgleichung

Reaktionsgleichung von HRID 917756
[F:1][C:2]1[CH:8]=[C:7]([C:9]([F:21])([F:20])[C:10]([F:19])([F:18])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:23]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:26]=[C:25]([Cl:34])[CH:24]=1.Cl>CCO>[Cl:34][C:25]1[CH:24]=[C:23]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([C:9]([F:20])([F:21])[C:10]([F:18])([F:19])[C:11]([F:16])([F:17])[C:12]([F:14])([F:15])[F:13])=[CH:8][C:2]=2[F:1])[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:26]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylateHCID 236309102-Fluoro-4-(nonafluorobutyl)aniline

Produkt 1

HCID 23631003Ethyl 6-chloro-4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]nicotinateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl) aniline and ethyl 4,6-dichloronicotinate were reacted in a mixture of EtOH and conc. HCl for 36 h as for example 33, step A. The resultant solid was purified by flash chromatography on silica gel (Hexane—10% EtOAc/Hexane gradient elution) to give ethyl 6-chloro-4-[2-fluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)anilino]nicotinate (30%). 1H NMR [400 MHz, CDCl3] δ 10.11 (br s, 1H), 8.86 (s, 1H), 7.57 (t, J=8.0 Hz, 1H), 7.46 (d, J=9.7 Hz, 2H), 6.98 (d, J=0.7 Hz, 1H), 4.44 (q, J=7.1 Hz, 2H), 1.44 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. customThe resultant solid was purified by flash chromatography on silica gel (Hexane—10% EtOAc/Hexane gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-9ac626bc22f244ae95eb51bffae07469
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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