Hydrazine hydrate (1:1) → 2-Hydrazino-5-(methoxymethyl)pyridine

HRID 1913184Notes

Reaction equation

HRID 1913184 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:10])=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>C(O)C>[NH:12]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:10])=[CH:4][N:3]=1)[NH2:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 190109212-Chloro-5-(methoxymethyl)pyridine

Product 1

HCID 592802102-Hydrazino-5-(methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.2 g (14.0 mmol) of the compound from Example 12A are initially charged in 10 ml of ethanol. 7.0 g (140.0 mmol) of hydrazine hydrate are added, and the mixture is stirred under reflux for 16 h. The reaction mixture is then reacted again in a single-mode microwave oven (CEM Explorer) at 150° C. for 2 h. The mixture is then concentrated on a rotary evaporator, taken up in ethyl acetate, washed once with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated again, and the residue is dried under high vacuum.

Workup

  1. temperatureunder reflux for 16 h
  2. customThe reaction mixture is then reacted again in a single-mode microwave oven (CEM Explorer) at 150° C. for 2 h
  3. concentrationThe mixture is then concentrated on a rotary evaporator
  4. washwashed once with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated again
  7. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-784174eef9d0457d97a5f43fbc95686d
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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