Hydrazine hydrate (1:1) → 5-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-one

HRID 221982Notes

Reaction equation

Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:6](=[O:20])[N:7]2NC(OC(C)(C)C)=O.O.[NH2:28][NH2:29]>O1CCOCC1>[NH:28]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:6](=[O:20])[NH:7]2)[NH2:29]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 5-chloro-2-oxo-3-phenyl-1,6-naphthyridine-1(2H)-carbamate (2-2) (2.0 g, 5.6 mmol) and hydrazine hydrate (7.2 g, 112 mmol) in 1,4-dioxane (28 mL) was heated under microwave irradiation at 120° C. for 20 minutes. The solvent was removed under reduced pressure, and water was added to the residue. The resulting solid was collected by filtration to give 5-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-one (2-3) as a colorless solid.

Workup

customThe solvent was removed under reduced pressure, and water
additionwas added to the residue
filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-fc59b8049f13433788283df3171d4b05
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207169B2

Reaction notes

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