Ammonium Hydroxide → Methyl-6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate

HRID 1091867Notes

Reaction equation

HRID 1091867 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]2[C:11]3[C:12](Cl)=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:9]=2[C:8]([O:19][CH:20]([F:22])[F:21])=[CH:7][CH:6]=1)=[O:4].[OH-].[NH4+].[H][H]>CO.CN(C)C=O.O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:9]=2[C:8]([O:19][CH:20]([F:22])[F:21])=[CH:7][CH:6]=1)=[O:4]

Participants

8

Reactant 3

HCID 14923Ammonium HydroxideHCID 86656265Methyl-1-chloro-6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66592827Methyl-6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Methyl-1-chloro-6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate (8.0 g), ammonium hydroxide (2.0 mL) and 10% Pd/C (4.0 g) in a mixture of methanol (100 mL) and dimethylformamide (5.0 mL) was hydrogenated in a Parr apparatus at 40-45 psi of hydrogen for 5-6 hrs. catalyst was removed by filtration and residue obtained was diluted with water. The solid product obtained was filtered and dried. Yield=6.5 g.

Workup

  1. customcatalyst was removed by filtration and residue
  2. customobtained
  3. customThe solid product obtained
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-aff3cad69e164e15a127805d778ab886
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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