Trimethyl orthoformate → HCID 86660795, compound

HRID 523866Notes

Reaction equation

HRID 523866 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:8](OC)(OC)[O:9]C>O>[CH3:8][O:9][N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH2:3]1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 100093-Aminopyridine

Product 1

HCID 86660795HCID 86660795, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-aminopyridine (7.14 g, 0.076 mol) and trimethyl orthoformate (40 mL) was refluxed for approximately 60 hr. To the cooled reaction mixture was added water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine and dried with MgSO4. The suspension was filtered and concentrated to yield the 3-methoxyiminopyridine as a white solid (9.3 g, 90%).

Workup

  1. temperaturewas refluxed for approximately 60 hr
  2. customTo the cooled reaction mixture
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationThe suspension was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0c9da63d19604af5a4526cbde33e2416
Source dataset
uspto-grants-2016_05
Patent number
US09340498B2

Reaction notes

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