Ammonium formate → HCID 68027926, compound

HRID 2171247Notes

Reaction equation

HRID 2171247 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[N:15]=[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])[C:13]([F:21])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>[Pd].CO>[F:21][C:13]1[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[N:15][CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89546986HCID 89546986, compound

Product 1

HCID 68027926HCID 68027926, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (200 mg) and ammonium formate (200 mg) were added to an MeOH (10 ml) solution containing methyl 2-chloro-5-fluoro-6-(2-methoxyethoxy)nicotinate (1.07 g) obtained in the 1st step, followed by reflux for 1 hour. Next, insoluble matter was removed using Celite. The solvent was distilled away under reduced pressure. Then, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:5). A white solid of methyl 5-fluoro-6-(2-methoxyethoxy)nicotinate (264 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. temperatureby reflux for 1 hour
  3. customNext, insoluble matter was removed
  4. distillationThe solvent was distilled away under reduced pressure
  5. customThen, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:5)

Sources & evidence

ORD record
ord-7943c6b2f77d4b12960b5ee4a326e619
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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