Hydrochloric Acid → Ethyl 6-chloro-4-[(1-chloro-2-naphthyl)amino]nicotinate

HRID 917762

Reaktionsgleichung

Reaktionsgleichung von HRID 917762
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:12].Cl[C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:17]=[C:16]([Cl:25])[CH:15]=1.Cl>CCO>[Cl:25][C:16]1[CH:15]=[C:14]([NH:12][C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[Cl:1])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4180141-Chloro-naphthalen-2-ylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Produkt 1

HCID 86596381Ethyl 6-chloro-4-[(1-chloro-2-naphthyl)amino]nicotinateAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-Chloro-2-naphthalenamine and ethyl 4,6-dichloronicotinate were reacted in a mixture of EtOH and conc. HCl as described for example 33, step A. The resultant solid was isolated by filtration and washed with 10% Et2O/Hexane, giving ethyl 6-chloro-4-[(1-chloro-2-naphthyl)amino]nicotinate (22%). 1H NMR [400 MHz, (CD3)2SO] δ 10.07 (br s, 1H), 8.75 (s, 1H), 8.23 (d, J=8.7 Hz, 1H), 8.09-8.05 (m, 2H), 7.77-7.71 (m, 2H), 7.66 (ddd, J=8.0, 6.9, 1.1 Hz, 1H), 6.75 (s, 1H), 4.41 (q, J=7.1 Hz, 2H), 1.38 (t, J=7.1 Hz, 3H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-41eac600cc0940eb9f98f81080fb75ac
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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