Piperidine → 7,8-Dihydro-6-(4-acetamidophenyl)methylidene-3-methylquinolin-5-one

HRID 1290975Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:12])[C:10]=2[CH:11]=1.[C:13]([NH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)(=[O:15])[CH3:14].N1CCCCC1>C(OCC)(=O)C>[C:13]([NH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[C:8]2[CH2:7][CH2:6][C:5]3[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=3[C:9]2=[O:12])=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 110 °C

Procedure

7,8-Dihydro-3-methylquinoline-5[6H]one (8 g) was mixed with 4-acetamidobenzaldehyde (9 g) and piperidine (0.5 ml) and heated at 110° C. for 3 hours. Ethyl acetate (30 ml) was added to the hot reaction mixture and the mixture allowed to cool. Crystals formed and were isolated by filtration, then washed with diethyl ether to give the title compound (11.2 g). A portion was recrystallised from ethyl acetate to give an analytical sample, mp 226°-228° C.

Workup

temperatureto cool
customCrystals formed
customwere isolated by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-3fde01d13b2c4c5184966492113c001c
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753676

Reaction notes

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