Hydrazine hydrate (1:1) → 5-Bromonicotinohydrazide
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].O.[NH2:13][NH2:14]>C(O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([NH:13][NH2:14])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution methyl 5-bromonicotinate (5 g, 23 mmol) in ethanol (40 mL) was added hydrazine hydrate (6 mL, 115 mmol). The reaction mixture was refluxed at 90° C. for 4 h. After this time, the reaction mixture was evaporated to dryness and then redissolved in ethyl acetate. The organic layer was washed with water, dried and evaporated to yield 5-bromonicotinohydrazide (3.4 g, 72%). LCMS Method T: retention time 0.573 min; [M+1]=216.0, 218.0.
Workup
- customAfter this time, the reaction mixture was evaporated to dryness
- dissolutionredissolved in ethyl acetate
- washThe organic layer was washed with water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-89814d60c06e40f89d74e7faefc59bf7
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575184B2
Reaction notes
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