Hydrazine → 4-Chloro-6-hydrazinylquinolin-2(1H)-one

HRID 217217Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[Cl:13].[N:14]([O-])=O.[Na+].O.O.Cl[Sn]Cl.NN>Cl.O>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][NH2:14])[CH:3]=2)[NH:8][C:7](=[O:12])[CH:6]=1

Participants

Conditions

Temperature: -1 °C

Procedure

In a 250 mL round bottomed flask a suspension of 6-amino-4-chloroquinolin-2(1H)-one (structure 1 of Scheme I, where RA=chloro) (1.94 g, 10 mmol) in 10 mL conc. HCl was cooled to −1° C. and a solution of NaNO2 (0.40 g, 12 mmol) in water (5 mL) was added dropwise over 20 min. The resulting dark yellow suspension was stirred at −1° C. for 2 hours and then a solution of SnCl2.2H2O (5.2 g, 15 mmol) in concentrated HCl (10 mL) was added dropwise over 10 minutes. The resulting light yellow suspension of the hydrazine was stirred at −1° C. for 2 hours and then used directly or stored in a refrigerator at −1° C. until it was used (the crude compound can be stored for at least one month without decomposition).

Workup

stirringwas stirred at −1° C. for 2 hours
customstored in a refrigerator at −1° C. until it
waitcan be stored for at least one month without decomposition

Sources & evidence

ORD record: ord-846dee6b9ccf482c85018ca8564d8aa3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193357B2

Reaction notes

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