Hydrazine hydrate (1:1) → HCID 66690636, compound

HRID 592296Notes

Reaction equation

HRID 592296 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].O.[NH2:17][NH2:18]>C(O)C>[Cl:1][C:2]1[C:3]([NH:17][NH2:18])=[N:4][CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10933837HCID 10933837, compound

Product 1

HCID 66690636HCID 66690636, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 5,6-dichloronicotinate (32.3 g, 130 mmol)) in ethanol (651 mL) was added hydrazine hydrate (19 mL, 391 mmol). The mixture was heated 75° C. After 2.5 h, the mixture was cooled to ambient temperature. The mixture was concentrated down to 200 mL of ethanol. The solid crashed out was filtered and washed with dichloromethane to give the hydrochloride salt of the title compound (29 g): LC-MS [M+1]=244.1.

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. concentrationThe mixture was concentrated down to 200 mL of ethanol
  3. filtrationThe solid crashed out was filtered
  4. washwashed with dichloromethane

Sources & evidence

ORD record
ord-e8342a698cfb42e9bef38eb967d04cbd
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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