Pyridine → HCID 19907933, compound

HRID 1534765Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

In a 200 ml-three-necked flask, 1.77 g (12.3 mM) of heptanohydrazide, 3,23 g (13.0 mM) of 6-acetoxy-2-naphthoyl chloride prepared in the same manner as in Example 3 and 90 ml of dioxane were placed and heated to about 80° C. To the mixture, 5.0 ml of pyridine was added at about 80° C. under stirring, followed by heating to 90°-92° C. and stirring for 1 hour at 90°-92° C. After the reaction, the reaction mixture was cooled on an iced water bath and poured into 350 ml of iced water to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and recrystallization from a mixture solvent (acetoneethyl acetate) to obtain 3.23 g of N-heptanoyl-N'-(6-acetoxy-2-naphthoyl)hydrazine (Yield: 75.4 %) ##STR137##

Workup

temperatureby heating to 90°-92° C.
stirringstirring for 1 hour at 90°-92° C
customAfter the reaction
temperaturethe reaction mixture was cooled on an iced water bath
customto precipitate a crystal
filtrationThe crystal was recovered by filtration
washby washing with water and recrystallization from a mixture solvent (acetoneethyl acetate)

Sources & evidence

ORD record: ord-0e78f13426954d7d8fda576566d30c21
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091109

Reaction notes

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