Hydrazine hydrate (1:1) → HCID 59280221, compound

HRID 242248Notes

Reaction equation

HRID 242248 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10](Cl)=[N:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].O.[NH2:15][NH2:16]>C(O)C>[C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:15][NH2:16])=[N:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 29001017HCID 29001017, compound

Product 1

HCID 59280221HCID 59280221, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.9 g (39.6 mmol) 5-(tert-butoxymethyl)-2-chloropyridine together with 19.8 g (395.6 mmol) hydrazine hydrate are divided into three portions of equal size and 15 ml ethanol are added to each portion. Each portion is reacted in a single mode microwave (CEM Explorer) at 170° C. for in each case 4 h. Thereafter, the three mixtures are combined and the solvent is removed. The residue is taken up in ethyl acetate and the mixture is washed once with saturated sodium bicarbonate solution. The aqueous phase is extracted once with ethyl acetate. The two ethyl acetate phases are combined and washed once with saturated sodium chloride solution. The mixture is dried over magnesium sulfate and the solvent is removed. The residue obtained is stirred in petroleum ether and the solid is filtered off.

Workup

  1. additionare added to each portion
  2. customEach portion is reacted in a single mode microwave (CEM Explorer) at 170° C. for in each case 4 h
  3. customthe solvent is removed
  4. washthe mixture is washed once with saturated sodium bicarbonate solution
  5. extractionThe aqueous phase is extracted once with ethyl acetate
  6. washwashed once with saturated sodium chloride solution
  7. dry with materialThe mixture is dried over magnesium sulfate
  8. customthe solvent is removed
  9. customThe residue obtained
  10. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-4cbfe43d8f454d0c9c9cf69890b8e595
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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