Hydrochloric Acid → HCID 178486758, Verbindung

HRID 445437

Reaktionsgleichung

Reaktionsgleichung von HRID 445437
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([O:16][CH3:17])=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19].C[O-].[Na+].[CH:24](OCC)=O.Cl>COCCOC.O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:18]([OH:20])=[CH:19][CH:24]=[N:1]2)=[CH:4][C:5]=1[O:16][CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 10942334Sodium Methoxide2×HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

Produkt 1

HCID 178486758HCID 178486758, VerbindungAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-Amino-4-benzyloxy-5-methoxy-phenyl)-ethanone (108 mmol, 29.3 g) in DME (700 ml) was added sodium methoxide (432 mmol, 23.35 g). The mixture was stirred for 30 minutes. Ethyl formate (540 mmol, 44 ml) was added and the mixture was stirred overnight. (Additional sodium methoxide may be needed if reaction is not complete as monitored by LC/MS.) After the reaction was completion, the mixture was diluted with water (40 ml) and acidified to neutral with 1M HCl. The precipitate was filtered and washed with water, dried in vacuo to afford 22 g (72%) of 7-benzyloxy-6-methoxy-quinolin-4-ol. 1H NMR (CDCl3): 10.7 (1H, br), 7.703 (1H, s), 7.493-7.461 (1H, t), 7.431-7.413 (2H, br d), 7.372-7.333 (2H, t), 7.296-7.283 (1H, d), 6.839 (1H, s), 6.212-6.193 (1H, d), 5.212 (2H, s), 3.965 (3H, s). LC/MS (M+1=282).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-beb0ffcb1cf9429891731164fd82ee4d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476298B2

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