Ammonium Chloride → HCID 58315448, compound

HRID 1483122Notes

Reaction equation

HRID 1483122 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]1[CH2:10][N:9]([C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-])=O)=[N:15][CH:16]=2)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>C(O)C.[Fe]>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]1[CH2:8][N:9]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58315456HCID 58315456, compound

Product 1

HCID 58315448HCID 58315448, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 5-[3-(tert-butyl-dimethyl-silanyloxy)-azetidin-1-yl]-2-nitro-pyridine (124 mg, 0.401 mmol) in 5 mL of ethanol is added iron powder (206 mg, 3.68 mmol) then 2 mL of NH4Cl solution. The resulting mixture is heated at 80° C. for 3 h and filtered through celite and concentrated. The resulting dark solid is divided between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×50 mL). The combine organic layers are ished with brine, dried over Na2SO4 and concentrated to give 5-[3-(tert-butyl-dimethyl-silanyloxy)-azetidin-1-yl]-pyridin-2-ylamine (105 mg, 94%).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated
  3. extractionThe aqueous phase is extracted with ethyl acetate (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5c599e080e14df887ab5de3d82f1b07
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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