Ethyl Acetate → HCID 15347365, compound

HRID 895535Notes

Reaction equation

HRID 895535 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([N+:10]([O-])=O)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].C(OCC)(=O)C>[Pd].CO>[NH2:10][C:5]1[C:4]([NH:3][CH2:1][CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 22380321HCID 22380321, compound

Product 1

HCID 15347365HCID 15347365, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-ethylamino-2-nitro-pyridine (400 mg), 10% palladium on carbon (40 mg) and 1:1 ethyl acetate:methanol (30 mL) were placed in a Parr apparatus under hydrogen (50 psi) for 50 min. The mixture was filtered through Celite, concentrated, and the product triturated with hexane to give 2-Amino-3-ethylaminopyridine as a brown solid. More material was recovered from the filtrate. 1H NMR (CDCl3): δ 7.59 (d, J=4.94 Hz, 1H), 6.81 (d, J=6.32 Hz, 1H), 6.71 (dd, J=4.94, 7.69 Hz, 1H), 3.12 (q, J=7.14 Hz, 2h), 1.31 (t, J=7.14 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customthe product triturated with hexane

Sources & evidence

ORD record
ord-698d89463a23455684e847e47edbb103
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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