Hydrochloric Acid → HCID 66623234, compound

HRID 415051Notes

Reaction equation

HRID 415051 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[O:7][CH2:8][C:9]([O-:11])=[O:10])([O-])=O.[CH2:18]1COC[CH2:19]1.[H][H].[ClH:25]>[Ni].CO.O1CCOCC1.CCO>[ClH:25].[ClH:25].[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[NH2:15])[O:7][CH2:8][C:9]([O:11][CH2:18][CH3:19])=[O:10]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 86642028HCID 86642028, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66623234HCID 66623234, compoundYield 83%

Reagents, catalysts & solvents 4

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

Procedure

To a Parr hydrogenation bottle was added 13.0 g of 2-(3,4-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 through a plug of 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 ethyl 2-(3,4-diaminophenoxy)acetate dihydrochloride (8.5 g, 83%), and was used directly in the next step without any further purification. MS (EI): 276 (MH+).

Workup

  1. filtrationThe catalyst was filtered through a plug of 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-660c9aeaca7641ab81f0bdd0ee4b0477
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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