Hydrochloric Acid → HCID 86642031, compound

HRID 415097Notes

Reaction equation

HRID 415097 reaction equation
[N+:1]([C:4]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([O-:10])=[O:9])([O-])=O.[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1.[H][H].[ClH:25]>[Ni].CO.O1CCOCC1.CCO>[ClH:25].[ClH:25].[NH2:1][C:4]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:22][CH2:18][CH2:19][CH3:20])=[O:9]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 86642033HCID 86642033, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86642031HCID 86642031, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a Parr hydrogenation bottle was added 12.0 g of 2-(2,3-dinitrophenoxy)acetate, Raney Nickel (2.0 g, wet), THF (100 mL) and EtOH (150 mL). The atmosphere of the vessel was replaced by hydrogen gas. The reaction was shaken on a Parr hydrogenator at 40 psi at room temperature, overnight. The catalyst was filtered over a plug Celite and the filtrate was concentrated under reduced pressure to give a residue, which was dissolved in methanol, acidified with 4 N hydrogen chloride in 1,4-dioxane and filtered. The resulting filtrate was concentrated under reduced pressure to give tent-butyl 2-(2,3-diaminophenoxy)acetate dihydrochloride (8.7 g, 82%), and was used directly in the next step without any further purification. MS (EI): 239 (MH+).

Workup

  1. filtrationThe catalyst was filtered over a plug Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue, which
  4. filtrationfiltered
  5. concentrationThe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22a45bf41dbb4c9e85f71480dfb0669c
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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