Pyridinium chloride → 3-Hydroxy-5-methoxy4-nitrophenylacetic acid

HRID 1357864Notes

Reaction equation

HRID 1357864 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[C:7]([O:12]C)[C:8]=1[N+:9]([O-:11])=[O:10].Cl.N1C=CC=CC=1>>[OH:12][C:7]1[CH:6]=[C:5]([CH2:14][C:15]([OH:17])=[O:16])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[N+:9]([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 181881093,5-Dimethoxy-4-nitrophenylacetic acid

Product 1

HCID 181880853-Hydroxy-5-methoxy4-nitrophenylacetic acid

Conditions

Temperature
145 °C

Procedure

A stirred mixture of 3,5-dimethoxy-4-nitrophenylacetic acid (0.4 g, Reference Example 13) and pyridine hydrochloride (6 g) was heated at 145° C., under argon, for 4 hours. The cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, then with brine, then dried and then evaporated to give a 1:1 mixture of the title compound and starting material (0.37 g) which was used without further purification.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. dry with materialwith brine, then dried
  5. customevaporated
  6. customto give

Sources & evidence

ORD record
ord-706dd62df9ea4df4967deb8537e689d2
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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