Ammonium Chloride → HCID 43152124, compound

HRID 1773580Notes

Reaction equation

HRID 1773580 reaction equation
C([Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[N+:20]([O-])=O)(C)C)(C)(C)C.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[O:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58056258HCID 58056258, compound

Product 1

HCID 43152124HCID 43152124, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl-[3-(4-chloro-2-nitro-phenoxy)-propoxy]-dimethyl-silane (0.37 g, 1.07 mmol), in a mixture of ethanol (10 mL) and water (3 mL), were added ammonium chloride (0.3 g, 5.37 mmol) and iron powder (0.3 g, 5.6 mmol) and the resulting mixture was heated at 80° C. overnight. The solid was filtered through a CELITE™ pad, the filter cake was washed with ethyl acetate. The filtrate was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug to give 0.188 g (87% yield) of 3-(2-amino-4-chloro-phenoxy)-propan-1-ol as a yellow oil.

Workup

  1. filtrationThe solid was filtered through a CELITE™ pad
  2. washthe filter cake was washed with ethyl acetate
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified on a silica gel plug

Sources & evidence

ORD record
ord-f4a43d49964247419608e92a0a09d7d8
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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