Hydrazine hydrate (1:1) → Tert-butyl 2-chloro-6-hydrazinoisonicotinate

HRID 592302Notes

Reaction equation

HRID 592302 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13](Cl)[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].O.[NH2:17][NH2:18]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([NH:17][NH2:18])[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22594123tert-Butyl 2,6-dichloropyridine-4-carboxylate

Product 1

HCID 86663126Tert-butyl 2-chloro-6-hydrazinoisonicotinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 2,6-dichloroisonicotinate (11.0 g, 44.3 mmol) in ethanol (222 mL) was added hydrazine hydrate (6.46 mL, 133 mmol). The mixture was heated 75° C. After 18 h, the mixture was cooled to ambient temperature. The mixture was concentrate down to half of the volume. The solid crashed out was filtered off and the filtrate was concentrated to dryness: LC-MS [M+1]=244.1.

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. concentrationThe mixture was concentrate down to half of the volume
  3. filtrationThe solid crashed out was filtered off
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-d67b05ebaec347e0ab1353b2aaa53272
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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