Benzaldehyde → 4-hydroxy-3-methoxy-N-[1-oxo-2-phenylmethylidene-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide

HRID 7084

Reaktionsgleichung

Reaktionsgleichung von HRID 7084
[C:1]1([C:7]2C=C(C=CC=2)N)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.NC1C=C2C(CCCC2=O)=CC=1.[OH:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([NH:36][C:37]2[CH:46]=[C:45]3[C:40]([CH2:41][CH2:42][CH2:43][C:44]3=[O:47])=[CH:39][CH:38]=2)=[O:35])=[CH:29][C:28]=1[O:48][CH3:49].C(=O)C1C=CC=CC=1>Cl.C(O)C>[OH:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([NH:36][C:37]2[CH:46]=[C:45]3[C:40]([CH2:41][CH2:42][C:43](=[CH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:44]3=[O:47])=[CH:39][CH:38]=2)=[O:35])=[CH:29][C:28]=1[O:48][CH3:49]

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 67097493-(Cyclohexen-1-yl)aniline2×HCID 220196594-hydroxy-3-methoxy-N-[1-oxo-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide

Produkt 1

HCID 696639674-hydroxy-3-methoxy-N-[1-oxo-2-phenylmethylidene-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21887872Ethanol hydrochlorideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Instead of 3-(cyclohexen-1-yl)aniline (Intermediate 2) in Example 9, 7-amino-1-tetralone is treated in a similar manner to Example 9. The resulting 4-hydroxy-3-methoxy-N-[1-oxo-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide (1 g) is dissolved in 30% hydrogen chloride-ethanol (5 ml), and thereto is added benzaldehyde (433 mg). The mixture is stirred at 25° C. for 18 hours. The precipitated crystals are collected by filtration, and washed with diethyl ether to give the desired compound (700 mg).

Aufarbeitung

  1. filtrationThe precipitated crystals are collected by filtration
  2. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-18b1747dcc8a42479959da4aec8199c0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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