Ethanol → Methyl 6-amino-5-[(2-fluorobenzyl)oxy]nicotinate

HRID 64408Notes

Reaction equation

HRID 64408 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]([N+:16]([O-])=O)=[N:8][CH:9]=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12].C(O)C.O.[Cl-].[NH4+]>C1COCC1.[Fe]>[NH2:16][C:7]1[C:6]([O:5][CH2:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=2[F:1])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 86713415Methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate

Product 1

HCID 86713416Methyl 6-amino-5-[(2-fluorobenzyl)oxy]nicotinateYield 99.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.5 g of methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate in 25 ml of THF were added 50 ml of ethanol, 25 ml of water, 218 mg of ammonium chloride, and 1.37 g of iron, followed by heating to reflux for 2 hours. After leaving to be cooled at room temperature, the reaction mixture was filtered over Celite, and to the filtrate were added a saturated aqueous sodium hydrogen carbonate solution and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 2.25 g of methyl 6-amino-5-[(2-fluorobenzyl)oxy]nicotinate.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours
  3. customAfter leaving
  4. filtrationthe reaction mixture was filtered over Celite
  5. additionto the filtrate were added a saturated aqueous sodium hydrogen carbonate solution and chloroform
  6. customa layer separation operation
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aea80e7c2e7244078ef4af820641ff21
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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