Hydrazine hydrate (1:1) → (E)-(3,5-dibromo-4-pyridinyl)methylidenehydrazine

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:10])[C:7]=1[CH:8]=O.O.[NH2:12][NH2:13]>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:10])[C:7]=1/[CH:8]=[N:12]/[NH2:13]

Participants

Reactant 2

HCID 24654Hydrazine hydrate (1:1)

HCID 27629983,5-Dibromo-4-pyridinecarboxaldehyde

Product 1

HCID 57606852(E)-(3,5-dibromo-4-pyridinyl)methylidenehydrazineYield 50%

Conditions

Temperature: 120 °C

Procedure

In analogy to GP 1, 54 mg of 3,5-dibromo-pyridine-4-carbaldehyde (0.2 mmol, 1 eq; commercially available or prepared as described in U.S. Pat. No. 6,232,320 or WO2005110410) were dissolved in 1 mL 1-propyl alkohol, treated with 30 μL 80% hydrazine hydrate (0.61 mmol, 3 eq.) and heated to 120° C. for 30 min (employing a Biotage Initiator® microwave oven). The precipitate was filtered and washed with cold 1-propyl alkohol to yield 27 mg of the hydrazone (0.1 mmol, 50% yield).

Workup

customcommercially available or prepared
dissolution6,232,320 or WO2005110410) were dissolved in 1 mL 1-propyl alkohol
filtrationThe precipitate was filtered
washwashed with cold 1-propyl alkohol

Sources & evidence

ORD record: ord-ad75458ae0144b3da9a10cb5ebaab4d6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481539B2

Reaction notes

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