Water → 2-Cyano-3-(ethoxycarbonylmethoxy)pyridine

HRID 914954Notes

Reaction equation

HRID 914954 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[C:9]([C:14]([NH2:16])=O)=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:5])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)Cl>[C:14]([C:9]1[C:8]([O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:13][CH:12]=[CH:11][N:10]=1)#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 220385763-(Ethoxycarbonylmethoxy)picolinamide

Product 1

HCID 220385682-Cyano-3-(ethoxycarbonylmethoxy)pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(ethoxycarbonylmethoxy)picolinamide (5.1 g, 22.8 mmol) and triethylamine (6.68 ml, 47.9 mmol) in 100 ml of dry methylene chloride is added trifluoroacetic anhydride (6.77 ml, 47.9 mmol), dropwise, at ambient temperature under argon. After stirring for 16 hours, 100 ml of water is added. The organic phase is separated and washed with aqueous sodium hydrogen carbonate to neutral pH. After drying over sodium sulfate and evaporation, the residue is purified via flash chromatography on silica gel using a methylene chloride-ethanolic ammonia gradient (99:1 to 95:5) to give 3.90 g of 2-cyano-3-(ethoxycarbonylmethoxy)pyridine (87%).

Workup

  1. customat ambient temperature
  2. customThe organic phase is separated
  3. washwashed with aqueous sodium hydrogen carbonate to neutral pH
  4. dry with materialAfter drying over sodium sulfate and evaporation
  5. customthe residue is purified via flash chromatography on silica gel using a methylene chloride-ethanolic ammonia gradient (99:1 to 95:5)

Sources & evidence

ORD record
ord-9785a1b2796f4a44a592041b38a6072f
Source dataset
uspto-grants-2007_09
Patent number
US07265127B2

Reaction notes

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