Hydrochloric Acid → 5-(4-Methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ol hydrochloride

HRID 2220491

Reaktionsgleichung

Reaktionsgleichung von HRID 2220491
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:18][N:17]([CH3:19])[CH2:16][C:15]3[N:14]=[C:13]([OH:20])[CH:12]=[CH:11][C:10]2=3)=[CH:5][CH:4]=1.COC1C=CC2C(C3C=CC(OC)=CC=3)CN(C)CC=2N=1.[ClH:42]>>[ClH:42].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:18][N:17]([CH3:19])[CH2:16][C:15]3[N:14]=[C:13]([OH:20])[CH:12]=[CH:11][C:10]2=3)=[CH:7][CH:8]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 587718872-Methoxy-5-(4-methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridineHCID 178488753HCID 178488753, Verbindung

Produkt 1

HCID 1784887545-(4-Methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ol hydrochloride

Versuchsvorschrift

5-(4-Methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ol. A solution of 2-methoxy-5-(4-methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridine (1.75 g, 6.15 mmol) in 4 M HCl (100 mL) was heated at reflux for 5 h. The solution was concentrated to give 5-(4-methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ol hydrochloride. The salt was neutralized with satd. aq. NaHCO3, and extracted with DCM. The organic layer was concentrated to give the title compound (1.14 g, 68%) as the free base. MS (ESI): mass calcd. for C16H18N2O2, 270.33; m/z found, 271.4 [M+H]+. 1H NMR (CDCl3): 7.12-7.07 (m, 2H), 7.03 (d, J=9.3, 1H), 6.87-6.82 (m, 2H), 6.37 (d, J=9.3, 1H), 4.00-4.92 (m, 1H), 3.80 (s, 3H), 3.69-3.62 (m, 1H), 3.56-3.50 (m, 1H), 3.01-2.95 (m, 1H), 2.52-2.45 (m, 1H), 2.44 (s, 3H).

Aufarbeitung

  1. temperatureat reflux for 5 h
  2. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-b2b1c9505f224be0a86abfea76da7943
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417054B2

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