Hydrazine hydrate (1:1) → Benzyl 6-(hydrazinecarbonyl)pyridin-2-ylcarbamate

HRID 1040225Notes

Reaction equation

HRID 1040225 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[N:17]=[C:16]([C:18]([O:20]C)=O)[CH:15]=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:23][NH2:24]>C(O)C.C(#N)C>[NH:23]([C:18]([C:16]1[N:17]=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:13]=[CH:14][CH:15]=1)=[O:20])[NH2:24]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66848435Methyl 6-(benzyloxycarbonylamino)picolinate

Product 1

HCID 66848731Benzyl 6-(hydrazinecarbonyl)pyridin-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

The methyl 6-(benzyloxycarbonylamino)picolinate from step 1 was dissolved in ethanol (0.5 M), and hydrazine hydrate (15 mL, 310 mmol, 5.0 eq) was added. The solution was heated to reflux and stirred for 2 hours, then cooled to room temperature. The solvent was removed under reduced pressure to provide a yellow solid, which was suspended in acetonitrile, filtered, and the solid washed with acetonitrile to yield benzyl 6-(hydrazinocarbonyl)pyridin-2-ylcarbamate (17.5 g) as a white solid. The filtrate was concentrated and the precipitated solid filtered off and washed with acetonitrile to provide more benzyl 6-(hydrazinecarbonyl)pyridin-2-ylcarbamate. A total of 17.5 g of pure material was obtained.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customThe solvent was removed under reduced pressure
  4. customto provide a yellow solid, which
  5. filtrationfiltered
  6. washthe solid washed with acetonitrile

Sources & evidence

ORD record
ord-c491af0ddb7e4f15b5c62a743688c20a
Source dataset
uspto-grants-2013_10
Patent number
US08552196B2

Reaction notes

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