Pyridine → HCID 53419624, compound

HRID 1791344Notes

Reaction equation

HRID 1791344 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:6]([C:7]([NH2:9])=O)[CH:5]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:6]([C:7]#[N:9])[CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 59741301HCID 59741301, compound

Product 1

HCID 53419624HCID 53419624, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-methoxy-isophthalamic acid methyl ester (4.0 g, 19.1 mmol) in a dichloromethane (80 mL) at 0° C. was treated with pyridine (6.3 mL, 77.0 mmol) and then trifluoroacetic anhydride drop-wise (6.5 mL, 46 mmol). The reaction was stirred at 0° C. for 20 min. and then stirred overnight at room temperature. The reaction mixture was washed with water, 1.0 N HCl and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 3.6 g (98%) of 3-cyano-5-methoxy-benzoic acid methyl ester as a white solid.

Workup

  1. stirringstirred overnight at room temperature
  2. washThe reaction mixture was washed with water, 1.0 N HCl and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-49f67a00773e439ca0f77853451bc9f9
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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