Pyridine → 2-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-4,6-difluoro-benzoic acid

HRID 2039545Notes

Reaction equation

HRID 2039545 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11](Cl)=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[NH2:14][C:15]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:16]=1[C:17]([OH:19])=[O:18].N1C=CC=CC=1>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([NH:14][C:15]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:16]=3[C:17]([OH:19])=[O:18])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2756584Benzo(1,3)dioxol-5-yl-acetyl chlorideHCID 146519722-Amino-4,6-difluorobenzoic acid

Product 1

HCID 670429552-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-4,6-difluoro-benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of commercially available benzo[1,3]dioxol-5-yl-acetyl chloride (3.70 g, 18.70 mmol) in anhydrous dichloromethane (20 mL) was added 2-amino-4,6-difluoro-benzoic acid (2.20 g, 12.5 mmol). After the addition of pyridine (5 mL), the mixture was heated under microwave condition at 120° C. for 5 minutes. The solvent was evaporated and the residue was diluted with 2 N HCl solution to induce the precipitation of a brown solid which was filtered, washed with water and dried under vacuum at 50° C., to afford the title compound (3.34 g, 80% yield).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with 2 N HCl solution
  3. customthe precipitation of a brown solid which
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-5e24ede6074f47c08e249395e9bfe3d5
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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