Ethyl Acetate → 2,3-Diamino-4,6-dimethyl-5-pyridinecarbonitrile

HRID 53593Notes

Reaction equation

HRID 53593 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[C:5]([C:12]#[N:13])=[C:4]([CH3:14])[N:3]=1.Cl[Sn]Cl.C(OCC)(=O)C>C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:11])[C:5]([C:12]#[N:13])=[C:4]([CH3:14])[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 544200312-Amino4,6-dimethyl-3-nitro-5-pyridinecarbonitrile

Product 1

HCID 544635192,3-Diamino-4,6-dimethyl-5-pyridinecarbonitrileYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.16 g (6.04 mmol) of 2-amino-4,6-dimethyl-3-nitro-5-pyridinecarbonitrile (17) and 5.72 g (30.1 mmol) of SnCl2 in 15 mL of ethanol was heated at 70° C. for 1 h. The solution was evaporated and the residue was treated with 40% NaOH to pH=12. The mixture was filtered and the solid was dried to leave a yellow solid. The solid was stirred with ethyl acetate (100 mL) and the mixture was filtered. The filtrate was evaporated to leave a pale yellow solid (410 mg, 41%). 1H NMR (CDCl3), 2,334 (s, 3), 2.522 (s, 3), 3.151 (mb, 2), 4.65 (mb, 2).

Workup

  1. customThe solution was evaporated
  2. additionthe residue was treated with 40% NaOH to pH=12
  3. filtrationThe mixture was filtered
  4. customthe solid was dried
  5. customto leave a yellow solid
  6. filtrationthe mixture was filtered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-500f6cd57c9040be9a897d4896d29e02
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

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