Hydrazine hydrate (1:1) → 5-Bromo-6-methylpicolinimidohydrazide

HRID 717197Notes

Reaction equation

HRID 717197 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

HCID 24654Hydrazine hydrate (1:1)HCID 498187795-Bromo-6-methylpyridine-2-carbonitrile

Product 1

HCID 666076585-Bromo-6-methylpicolinimidohydrazideYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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

  1. stirringto stir over the weekend
  2. filtrationThe mixture was filtered
  3. washwashed with cold ethanol (100 mL) and cold hexanes (50 mL)
  4. customThe solids were dried in a vacuum oven

Sources & evidence

ORD record
ord-f19d1d08512b4455a6ca5e3ec32742fd
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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