Ethyl Acetate → 5-Amino-4-methylpyridine-2-carbonitrile

HRID 1811581Notes

Reaction equation

HRID 1811581 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]([C:11]#[N:12])[CH:3]=1.C(OCC)(=O)C>[NH4+].[Cl-].[Zn]>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:11]#[N:12])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 230001714-Methyl-5-nitropyridine-2-carbonitrile

Product 1

HCID 552898215-Amino-4-methylpyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

4-methyl-5-nitropicolinonitrile (7.0 g, 43 mmol) was suspended in aq. NH4Cl (200 mL) and cooled to 0° C. Zinc was added portionwise for 30 min and stirred for 1 hr. The reaction was added with ethyl acetate (200 mL) and stirred for 2 hrs. The reaction was filtered and the organic layer was taken up, dried over MgSO4, and concentrated over vacuum. The solid was triturated with 50% ethyl acetate in hexane to give 5-amino-4-methylpicolinonitrile in 67% (4.56 g). 1HNMR (CDCl3, 400 MHz) δ 7.98 (s, 1H), 7.21 (s, 1H), 5.42˜5.48 (b, 2H), 2.54 (s, 3H). Exact mass calculated for C7H7N3 133.15. found 134.21 (MH+).

Workup

  1. stirringstirred for 2 hrs
  2. filtrationThe reaction was filtered
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated over vacuum
  5. customThe solid was triturated with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e82037b960144d8c91df05c604d7768b
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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