Water → 6-Hydrazinyl-3-phenyl-1,5-naphthyridin-2(1H)-one

HRID 42372Notes

Reaction equation

HRID 42372 reaction equation
Cl[C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5]2.O.[NH2:20][NH2:21].CCOCC.O>N1C=CC=CC=1>[NH:20]([C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5]2)[NH2:21]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 665249196-Chloro-3-phenyl-1,5-naphthyridin-2(1H)-one

Product 1

HCID 670690086-Hydrazinyl-3-phenyl-1,5-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6-chloro-3-phenyl-1,5-naphthyridin-2(1H)-one (7-1) (1.4 g, 5.61 mmol) and hydrazine hydrate (2 g, 40 mmol) in pyridine (18 mL) was heated under microwave irradiation at 160° C. for 1.5 hours. To the mixture was added Et2O and water, and the resulting solid was collected by filtration to give 6-hydrazino-3-phenyl-1,5-naphthyridin-2(1H)one (7-2) as orange solid.

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-1743d55a84284d259933a725ef93c5da
Source dataset
uspto-grants-2013_09
Patent number
US08536193B2

Reaction notes

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