Hydrazine hydrate (1:1) → 5-Bromo-6-methylpicolinimidohydrazide
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8].O.[NH2:12][NH2:13]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9](=[N:12][NH2:13])[NH2:10])=[N:6][C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 500-mL, three-neck, round-bottom flask was equipped with 5-bromo-6-methylpicolinonitrile (101.5 g, 0.515 mol), ethanol (122 mL) and hydrazine hydrate (50 mL, 1.03 mol). The resulting very thick mixture was allowed to stir at ambient temperature for 24 h. More ethanol (50 mL) was added and the mixture was allowed to stir over the weekend. The mixture was filtered and washed with cold ethanol (100 mL) and cold hexanes (50 mL). The solids were dried in a vacuum oven to afford the product (110 g, 93% yield) as an off-white solid.
Workup
- stirringto stir over the weekend
- filtrationThe mixture was filtered
- washwashed with cold ethanol (100 mL) and cold hexanes (50 mL)
- customThe solids were dried in a vacuum oven
Sources & evidence
- ORD record
- ord-cca7ea12201f453cbe817d2a8bfe8dcf
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569494B2
Reaction notes
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