Ammonium formate → HCID 43376334, compound

HRID 2381690Notes

Reaction equation

HRID 2381690 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([N:12]([CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CCO.O.[Fe]>[CH2:1]([O:8][CH2:9][C:10]([N:12]([CH3:22])[C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 66877507HCID 66877507, compound

Product 1

HCID 43376334HCID 43376334, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of above 2-benzoxy-N-methyl-N-(4-nitrophenyl)acetamide in EtOH (8 mL) and H2O (4 mL) was added ammonium formate (1.3 g, 20 mmol) and Fe (0.47 g, 8.4 mmol). After heating at reflux for 2 h, the reaction was cooled to room temperature, iron was filtered off, and the filtrate was diluted with EtOAc and water, EtOAc layer was separated and the aqueous layer was further extracted with EtOAc, organic layers were combined, dried over Na2SO4, and was concentrated under vacuo to provide 2-benzoxy-N-methyl-N-(4-aminophenyl)acetamide (0.4 g, 53%).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. filtrationiron was filtered off
  4. additionthe filtrate was diluted with EtOAc and water, EtOAc layer
  5. customwas separated
  6. extractionthe aqueous layer was further extracted with EtOAc, organic layers
  7. dry with materialdried over Na2SO4
  8. concentrationwas concentrated under vacuo

Sources & evidence

ORD record
ord-5c87067505f145259b40bdef68e9303c
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

Loading…