Pyridine → HCID 21942451, compound

HRID 431863Notes

Reaction equation

HRID 431863 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([O:14][CH2:15][CH2:16][CH3:17])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([O:14][CH2:15][CH2:16][CH3:17])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 21942652HCID 21942652, compound

Product 1

HCID 21942451HCID 21942451, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of methyl 3-(aminocarbonyl)-5-propoxybenzoate (2.0 g, 8.2 mmol) in a dichloromethane (25 mL) at 0° C. was treated with pyridine (1.3 mL, 17 mmol) and then trifluoroacetic anhydride dropwise (1.4 mL, 9.9 mmol). The reaction was stirred at 0° C. for 20 minutes and then stirred overnight at ambient temperature. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Silica gel chromatography using a 40% dichloromethane/hexanes afforded 1.5 g (84%) of methyl 3-cyano-5-propoxybenzoate as a white solid.

Workup

  1. stirringstirred overnight at ambient temperature
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bdfec4dbd8b04a91a3f2bfe2c5dd9e73
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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