2-(2,4-dimethoxyphenyl)pyridine → HCID 135433735, compound

HRID 322944Notes

Reaction equation

HRID 322944 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>Cl.N1C=CC=CC=1.ClCCl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 1

HCID 108463432-(2,4-dimethoxyphenyl)pyridine

Product 1

HCID 135433735HCID 135433735, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10176127Pyridinium chlorideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(2,4-dimethoxyphenyl)pyridine (14 g) in pyridine hydrochloride (121 g) is heated to 160° C. and the resulting melt is heated at 160° C. for 7 hours. The mixture is then cooled, diluted with dichloromethane, washed with hydrochloric acid (2 M) and water, dried and evaporated. The residual oil is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (1:1 v/v), to give 2-(2,4-dihydroxyphenyl)pyridine (8.0 g) in the form of a solid, m.p. 170-172° C. [NMR(CDCl3):- 6.3(1H,s),6.4(1H,d),7.3(1H,m), 7.8(1H,d),7.9(1H,t),8.0(1H,d),8.5(1H,d).

Workup

  1. temperaturethe resulting melt is heated at 160° C. for 7 hours
  2. temperatureThe mixture is then cooled
  3. washwashed with hydrochloric acid (2 M) and water
  4. customdried
  5. customevaporated
  6. washeluting with a mixture of pentane and ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-a34cfc667f27469988281fcb680c67ad
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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