Hydrochloric Acid → Methyl 6-aminoquinoline-3-carboxylate dihydrochloride

HRID 1894957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894957
C(OC([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:12]2)=O)(C)(C)C.[ClH:23].O1CCOCC1>C(Cl)Cl>[ClH:23].[ClH:23].[NH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:12]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67002181Methyl 6-(tert-butoxycarbonylamino)quinoline-3-carboxylate

Produkt 1

HCID 67002244Methyl 6-aminoquinoline-3-carboxylate dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 6-[(tert-butoxycarbonyl)amino]quinoline-3-carboxylate (Int-2, 1.28 g, 4.23 mmol) in methylene chloride (38 mL) was added hydrochloric acid in 1,4-dioxane (4.0 M, 10.6 mL, 42.3 mmol). The reaction was stirred at room temperature overnight then concentrated under reduced pressure. The crude reside was dried in vacuo and used as obtained. LC-MS: (FA) ES+ 203; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.14 (s, 1H), 9.08 (d, J=1.8 Hz, 1H), 8.10 (d, J=9.1 Hz, 1H), 7.62 (dd, J=9.1, 2.4 Hz, 1H), 7.33 (d, J=1.7 Hz, 1H), 3.96 (s, 9H).

Aufarbeitung

  1. concentrationthen concentrated under reduced pressure
  2. customThe crude reside was dried in vacuo
  3. customas obtained

Quellen und Nachweise

ORD-Eintrag
ord-1d17512a48954b0083454f4a875fba2c
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513421B2

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