1,2-Dichloroethane → Tert-butyl 6-(2-benzoylhydrazino)-5-chloronicotinate

HRID 592297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592297
Cl.[Cl:2][C:3]1[C:4]([NH:16][NH2:17])=[N:5][CH:6]=[C:7]([CH:15]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:18]([NH:17][NH:16][C:4]1[C:3]([Cl:2])=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])=[CH:6][N:5]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 66690635Tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt

Produkt 1

HCID 66691260Tert-butyl 6-(2-benzoylhydrazino)-5-chloronicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt (3.0 g, 9.5 mmol) in N,N-dimethylformamide (20 mL) were added benzoic acid (1.62 g, 13.3 mmol), EDC (3.63 g, 19.0 mmol), HOAT (1.29 g, 9.48 mmol) and triethylamine (6.6 mL, 48.4 mmol). The reaction mixture was stirred at 60° C. After 1 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated: LC-MS [M+1]=348.1.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b50334c62ce842a4a29d15a613477e42
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238647B2

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