Hydrazine hydrate (1:1) → 5-hydrazino-1,6-naphthyridin-2(1H)-one monohydrochloride monohydrate
Reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:13])[NH:8]2)[NH2:2].O.[ClH:15].BrC1N=CC=C2C=1C=CC(=O)N2.O.NN>>[OH2:13].[ClH:15].[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:13])[NH:8]2)[NH2:2]Participants
Procedure
The above intermediate 5-hydrazino-1,6-naphthyridin-2(1H)-one as its monohydrochloride monohydrate was prepared as follows. A mixture containing 30 g of 5-bromo-1,6-naphthyridin-2(1H)-one and 20.2 ml of hydrazine hydrate was heated to reflux and then heated for an additional 2 hours. The reaction mixture was concentrated on a rotary evaporator and the residue was slurried in concentrated hydrochloric acid. The solid was collected, washed with concentrated hydrochloric acid, dried in a vacuum oven at 75° C. The solid was then slurried in water, collected by filtration, washed with water and dried in a vacuum oven at 90° C. to yield 25.2 g of 5-hydrazino-1,6-naphthyridin-2(1H)-one monohydrochloride monohydrate, m.p. >310° C. with decomposition.
Workup
- temperaturewas heated
- temperatureto reflux
- temperatureheated for an additional 2 hours
- concentrationThe reaction mixture was concentrated on a rotary evaporator
- customThe solid was collected
- washwashed with concentrated hydrochloric acid
- customdried in a vacuum oven at 75° C
- filtrationcollected by filtration
- washwashed with water
- customdried in a vacuum oven at 90° C.
Sources & evidence
- ORD record
- ord-c8fd66507065413c8e03cf3333707987
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04716170
Reaction notes
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