2-Chloro-4-hydrazinylbenzonitrile hydrochloride → HCID 68010258, compound

HRID 1844837Notes

Reaction equation

HRID 1844837 reaction equation
[CH:1]1([CH:6]=[C:7]2[CH2:16][CH2:15][C:14]3[N:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:10][C:9]=3[C:8]2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:23][C:24]1[CH:31]=[C:30]([NH:32][NH2:33])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]>C(O)C>[Cl:23][C:24]1[CH:31]=[C:30]([N:32]2[CH:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]3[C:8]([C:9]4[CH:10]=[CH:11][C:12]([C:17]([O:19][CH3:20])=[O:18])=[N:13][C:14]=4[CH2:15][CH2:16]3)=[N:33]2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

4

Reactant 2

HCID 221118492-Chloro-4-hydrazinylbenzonitrile hydrochlorideHCID 77385832HCID 77385832, compound

Product 1

HCID 68010258HCID 68010258, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a dried reaction flask, methyl 6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydroquinoline-2-carboxylate (1.552 g, 5.44 mmol) and 2-chloro-4-hydrazinobenzonitrile hydrochloride (1.437 g, 7.04 mmol) were dissolved in ethanol (55 mL). In the protection from light and under the nitrogen atmosphere, the solution was stirred at 80° C. for 8 hr and at room temperature for 15 hr, and filtered to obtain a pale yellow solid (0.972 g) in 41.1% yield.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-96fa81f86f09432f87f3fb9633b2ecb0
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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