3,4,5-Trimethoxybenzaldehyde → 2-methoxy-2-quinolin-5-yl-N-[(E)-(3,4,5-trimethoxyphenyl)methylideneamino]acetamide

HRID 388263Notes

Reaction equation

[CH3:1][O:2][CH:3]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2)[C:4]([NH:6][NH2:7])=[O:5].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=O>C(O)C.C(O)(=O)C>[CH3:1][O:2][CH:3]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2)[C:4]([NH:6]/[N:7]=[CH:23]/[C:22]1[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:20]([O:19][CH3:18])[CH:21]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-methoxy-2-(quinolin-5-yl)acetohydrazide (0.149 g, 0.65 mmol) and 3,4,5-trimethoxybenzaldehyde (0.138 g, 0.70 mmol) in absolute ethanol (5 mL) was added acetic acid (1 drop). The mixture was heated at 60° C. for 17 hours. After cooling to room temperature, the solid was collected on a Büchner funnel and rinsed with ethanol and diethyl ether then dried in vacuo to give (E)-2-methoxy-2-(quinolin-5-yl)-N′-(3,4,5-trimethoxybenzylidene)acetohydrazide (6-1) as a white powder (0.197 g, 75% yield).

Workup

temperatureAfter cooling to room temperature
customthe solid was collected on a Büchner funnel
washrinsed with ethanol and diethyl ether
customthen dried in vacuo

Sources & evidence

ORD record: ord-76066729b8fa46638439f3efbd4e04b4
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377930B2

Reaction notes

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