Acetic Acid → N-[4-(1H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-ylidene]-hydrazine

HRID 2243307Notes

Reaction equation

O.[NH2:2][NH2:3].C(O)(=O)C.O.[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:11][C:10]=1[C:18]1[C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=O)[C:22]=2[CH:21]=[CH:20][CH:19]=1>CO.ClCCl>[NH:9]1[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[C:18]1[C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[N:2][NH2:3])[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 52.5 °C

Procedure

In a 10-ml round-bottomed flask, dissolve 100 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-one, obtained in Example 1, in 3 ml of methanol, then add successively 96 μL of hydrazine hydrate and 57.6 μL of acetic acid, then heat at 50-55° C. for 3 hours. Pour the cooled reaction mixture into 10 ml of water. Filter the precipitate that formed, and dissolve again in a mixture of methanol and dichloromethane. After drying over sodium sulphate then concentrating under reduced pressure, purify the residue by crystallization in a minimum of diethyl ether. In this way we obtain 70 mg of N-[4-(1H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-ylidene]-hydrazine, as a mixture of the Z and E isomers, in the form of a beige powder with the following characteristics:

Workup

additionPour
filtrationFilter the precipitate
customthat formed
dry with materialAfter drying over sodium sulphate
concentrationthen concentrating under reduced pressure
custompurify the residue
customby crystallization in a minimum of diethyl ether

Sources & evidence

ORD record: ord-f17b357871e24bb095451ddc10ee880a
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674795B2

Reaction notes

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