Ethyl Acetate → Acetic acid 2-(6-aminomethyl-2-nitropyridin-3-yloxy)-ethyl ester

HRID 15013Notes

Reaction equation

HRID 15013 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[N:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([O:22][CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])=[CH:15][CH:14]=1.O.NN.C(OCC)(=O)C>C(O)C>[NH2:3][CH2:12][C:13]1[N:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([O:22][CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 59341198HCID 59341198, compound

Product 1

HCID 59341182Acetic acid 2-(6-aminomethyl-2-nitropyridin-3-yloxy)-ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.35 gm (0.97 mmol) of Acetic acid 2-[6-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-nitro-pyridin-3-yloxy]-ethyl ester 97 in 5 mL of ethanol was added 0.051 mL (1.01 mmol) of hydrazine hydrate at room temperature. The reaction mixture was allowed to stir for 4 h. The mixture was then transferred with ethyl acetate and the solvent was removed at reduced pressure. The residue was taken up in CHCl3 (200 mL) and washed twice with water (100 mL), saturated brine, dried (Na2SO4), and the solvents removed under reduced pressure. This was used without further purification or characterization.

Workup

  1. customthe solvent was removed at reduced pressure
  2. washwashed twice with water (100 mL), saturated brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvents removed under reduced pressure
  5. customThis was used without further purification or characterization

Sources & evidence

ORD record
ord-161543088d4b45fdbc2f9dfd4438b41e
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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