Pyridine → HCID 22326675, compound

HRID 495434Notes

Reaction equation

HRID 495434 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=O.[N:12]1C=CC=[CH:14][CH:13]=1.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH3:11][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]2[C:3]=1[CH:4]=[N:12][C:13]([CH3:14])=[N:1]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 223267152-Amino-6-methoxybenzaldehyde

Product 1

HCID 22326675HCID 22326675, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-amino-6-methoxybenzaldehyde [K. Tsuda et al., Chem. Pharm. Bull. 1962, 10, 856] (1.3 g, 8.6 mmol), pyridine (0.81 g, 10.3 mmol) and toluene (60 mL) was added acetic anhydride (0.97 g, 9.5 mmol). The resulting mixture was heated at reflux for 18 h, cooled, then partitioned between saturated aqueous NaHCO3 (100 mL) and ether (50 mL). The organic phase was dried (Na2SO4) and evaporated in vacuo to give a solid which was purified by chromatography on silica with 0-50% ether in hexane gradient elution to give a colourless solid (1.28 g). The latter was dissolved in 2 M methanolic ammonia (100 mL) and the solution heated at reflux for 3 h, cooled, then evaporated in vacuo. Chromatography of the residue on silica with 0-100% ether in dichloromethane gradient elution gave the title compound (0.92 g, 62%) as a colourless solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. custompartitioned between saturated aqueous NaHCO3 (100 mL) and ether (50 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customto give a solid which
  8. customwas purified by chromatography on silica with 0-50% ether in hexane gradient elution

Sources & evidence

ORD record
ord-4d77b185639146b6ba1250fa2431021a
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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