HCID 21875453, compound → 5-Amino-3-methoxypyridine-2-carbonitrile

HRID 2378454Notes

Reaction equation

HRID 2378454 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[CH:5][N:4]=1)#[N:2]>CCOC(C)=O.CC(O)=O.[Fe]>[NH2:11][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

4

Reactant 1

HCID 21875453HCID 21875453, compound

Product 1

HCID 218753365-Amino-3-methoxypyridine-2-carbonitrileYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22609514Ethyl acetate acetateSolvent

Conditions

Temperature
65 °C

Procedure

2-Cyano-3-methoxy-5-nitropyridine (1.0 g, 5.6 mmol) was dissolved in 1:1 EtOAc/AcOH (10 mL) and heated to 65° C. Iron powder (1.61 g, 28 mmol, 325 mesh) was added and the mixture stirred for two h. The mixture was filtered though Celite and the filtrate concentrated in vacuo. The residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by SiO2 Prep-TLC using CH2Cl2 as the eluent to give the compound 762D (0.805 g, 97%) as an off-white solid. HPLC: 100% at 1.31 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 149.90 [M+H]+.

Workup

  1. filtrationThe mixture was filtered though Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by SiO2 Prep-TLC

Sources & evidence

ORD record
ord-cc8e27b55f35400d8996dcc6a6d39e4f
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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