Triethylamine → 6-Methoxy-2-pyridinecarbonitrile

HRID 1040424Notes

Reaction equation

HRID 1040424 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH2:11])=O)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]#[N:11])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 201849836-Methoxypyridine-2-carboxamide

Product 1

HCID 130236446-Methoxy-2-pyridinecarbonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 6-methoxy-pyridine-2-carboxylic acid amide (300 mg, 1.97 mmol) in THF (3 mL) were added triethylamine (1.25 mL, 8.68 mmol) and dropwise added TFAA (0.61 mL, 4.34 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The volatiles were concentrated in vacuo and the liquid residue was added dropwise to a vigorously stirred, ice cold, pH 7 phosphate buffer solution (5 mL). After 15 min of further stirring the yellowish solid was filtered and air dried for 1 h to yield 250 mg (95%) of 6-methoxy-pyridine-2-carbonitrile as yellowish solid, m/z 135.4 [M+1]+.

Workup

  1. concentrationThe volatiles were concentrated in vacuo
  2. additionthe liquid residue was added dropwise to
  3. stirringa vigorously stirred
  4. stirringAfter 15 min of further stirring the yellowish solid
  5. filtrationwas filtered
  6. customair dried for 1 h

Sources & evidence

ORD record
ord-1163420d0764436bbedaf7dba524e5f4
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…