Pyridine → HCID 21942451, compound

HRID 2216758Notes

Reaction equation

HRID 2216758 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-d1c52617c5a24ff9a4c716ffa9accfed
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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