Pyridine → N-heptanoyl-N'-(6-decyloxy-2-naphthoyl)hydrazine

HRID 1534757Notes

Reaction equation

[C:1]([NH:9][NH2:10])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:11]([O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([C:32](Cl)=[O:33])[CH:26]=[CH:25]2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O1CCOCC1.N1C=CC=CC=1>O>[C:1]([NH:9][NH:10][C:32]([C:27]1[CH:26]=[CH:25][C:24]2[C:29](=[CH:30][CH:31]=[C:22]([O:21][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:23]=2)[CH:28]=1)=[O:33])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 85 °C

Procedure

In a 50 ml-three-necked flask, 0.40 g (2.77 mM) of heptanohydrazide, 1.05 g (3.03 mM) of 6-decyloxy-2-naphthoyl chloride and 20 ml of dioxane were placed and heated to about 85° C. under stirring. To the mixture, 1.05 ml (13.0 mM) of pyridine was added, followed by heating to 90°-92° C. and stirring for 40 minutes at 90°-92° C. After the reaction, the reaction mixture was cooled and poured into 150 ml of iced water to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and further washing with acetone to obtain 1.21 g of N-heptanoyl-N'-(6-decyloxy-2-naphthoyl)hydrazine (Yield: 96.0%). ##STR28##

Workup

temperatureby heating to 90°-92° C.
stirringstirring for 40 minutes at 90°-92° C
customAfter the reaction
temperaturethe reaction mixture was cooled
customto precipitate a crystal
filtrationThe crystal was recovered by filtration
washby washing with water
washfurther washing with acetone

Sources & evidence

ORD record: ord-29487dcbe0ed44698c8ed54fd58ec408
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091109

Reaction notes

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