HCID 86720948, compound → HCID 86720949, compound

HRID 524893Notes

Reaction equation

HRID 524893 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-])=O)=[CH:4][N:3]=1>CC(O)=O.O.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:15])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 1

HCID 86720948HCID 86720948, compound

Product 1

HCID 86720949HCID 86720949, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-(2-chloro-5-nitro-4-pyridyl)-4-methyl-piperazine (580 mg, 2.260 mmol) was dissolved in AcOH (20 mL)/Water (2 mL) and Fe (2.524 g, 45.20 mmol) was added. The resulting mixture was stirred at 50° C. for 30 minutes. The reaction was cooled to ambient temperature then loaded onto 50 g SCX-2 cartridge (pre-washed with MeOH). The cartridge was washed with DCM/MeOH mixtures, before the product was eluted with 2M NH3 in MeOH/DCM mixtures. The solvent was removed in vacuo to give 6-chloro-4-(4-methylpiperazin-1-yl)pyridin-3-amine as a purple solid (510 mg, 99% Yield). MS (ES+) 227.1.

Workup

  1. additionwas added
  2. temperatureThe reaction was cooled to ambient temperature
  3. washthen loaded onto 50 g SCX-2 cartridge (pre-washed with MeOH)
  4. washThe cartridge was washed with DCM/MeOH mixtures, before the product
  5. washwas eluted with 2M NH3 in MeOH/DCM mixtures
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a3a25fe8edd642f89e972702a40ac5a9
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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