Hydrazine hydrate (1:1) → 3-Amino-6-bromopyrazine-2-carbohydrazide

HRID 78726Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.O.[NH2:14][NH2:15]>O1CCOCC1>[NH2:1][C:2]1[C:3]([C:9]([NH:14][NH2:15])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 3-amino-6-bromopyrazine-2-carboxylate (15 g, 64.6 mmol) was suspended in 150 mL of dioxane at room temperature. Hydrazine hydrate (6.5 g, 130 mmol) was added and the reaction mixture was stirred at 60° C. for 2 hours. Initially the mixture became clear, but after a while a precipitate formed. The mixture was cooled to ambient temperature and crude product filtered off. The solid was washed with TBME and subsequently stirred in water. The material was filtered and washed with acetone to afford 3-Amino-6-bromopyrazine-2-carbohydrazide 4 as slightly yellow solid. The material was dried in vacuo. (10.5 g, 70%).

Workup

customafter a while a precipitate formed
temperatureThe mixture was cooled to ambient temperature
filtrationcrude product filtered off
washThe solid was washed with TBME
stirringsubsequently stirred in water
filtrationThe material was filtered
washwashed with acetone

Sources & evidence

ORD record: ord-be4ae37bcf25498c950d1b45beb2a192
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841449B2

Reaction notes

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