Iodoethane → 6-Chloro-4-ethylamino-3-nitro-pyridine-2-carbonitrile

HRID 2246454Notes

Reaction equation

HRID 2246454 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([C:15]#[N:16])[C:9]=1[N+:17]([O-:19])=[O:18].[CH2:20](I)[CH3:21]>CN(C=O)C>[Cl:14][C:12]1[N:11]=[C:10]([C:15]#[N:16])[C:9]([N+:17]([O-:19])=[O:18])=[C:8]([NH:7][CH2:20][CH3:21])[CH:13]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 552704134-Amino-6-chloro-3-nitro-pyridine-2-carbonitrile

Product 1

HCID 866138696-Chloro-4-ethylamino-3-nitro-pyridine-2-carbonitrileYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At room temperature, potassium carbonate (3.06 g) was added by portions to a solution of 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (4.0 g) in DMF (60 mL). A solution of ethyl iodide (3.46 g) in DMF (20 mL) was added dropwise to the mixture, then stirred for 24 h at room temperature and concentrated under reduced pressure. The residue was partitioned between water (50 ml) and ethyl acetate (100 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (3×50 ml), then concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: dichloromethane) to afford the title compound (2.94 g) as yellow crystals (mp=120° C.). 1H NMR (DMSO-d6) δ: 8.67 (br. s, 1H); 7.46 (s, 1H); 3.51 (q, J=8 Hz, 2H); 1.21 (t, J=8 Hz, 3H). MS m/z: 227/229 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water (50 ml) and ethyl acetate (100 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  4. washThe combined organic layers were washed with brine (3×50 ml)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed over silica gel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-7589fec61db442b98197f4f1f3a87c92
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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