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

HRID 7084

Reaction equation

[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]

Participants

Conditions

Temperature: 25 °C

Procedure

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).

Workup

filtrationThe precipitated crystals are collected by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-18b1747dcc8a42479959da4aec8199c0
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084176B2

Linked notes

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