Hydrochloric Acid → HCID 10846382, compound

HRID 1844495Notes

Reaction equation

HRID 1844495 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>[Fe].C(O)C>[F:18][C:10]1[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][C:9]=1[NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10800431HCID 10800431, compound

Product 1

HCID 10846382HCID 10846382, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To 60 g (243.7 mmol) of the intermediate N-benzyl-2-fluoro-4-nitroaniline (3), 600 mL ethanol was added as a solvent. The resultant mixture was slowly heated to reflux and then 60 mL concentrated hydrochloric acid was added. After the reactant was completely dissolved, 55 g (974.6 mmol) of Fe powder was added in batches within 1 hour. Then, reflux was continued for five hours until the reaction almost completed. The mixture was cooled to room temperature and buffered to pH 8-9 with a saturated Na2CO3. Then, the mixture was filtrated, and the filtrate was evaporated to remove ethanol by rotatory evaporation. The residual water layer was extracted with ethyl acetate, and then the ethyl acetate layer was reversely extracted with 10% diluted hydrochloric acid solution. The ethyl acetate layer was discarded. The acid-water layer was adjusted to be basic with a NaOH solution and then extracted with ethyl acetate. Thus obtained ethyl acetate layer was rotary evaporated and 47 g of dark tan oily substance was obtained with a yield of 89.2%.

Workup

  1. temperatureto reflux
  2. dissolutionAfter the reactant was completely dissolved
  3. temperatureThen, reflux
  4. customwas continued for five hours until the reaction
  5. filtrationThen, the mixture was filtrated
  6. customthe filtrate was evaporated
  7. customto remove ethanol
  8. customby rotatory evaporation
  9. extractionThe residual water layer was extracted with ethyl acetate
  10. extractionthe ethyl acetate layer was reversely extracted with 10% diluted hydrochloric acid solution
  11. extractionextracted with ethyl acetate
  12. customThus obtained ethyl acetate layer was rotary evaporated
  13. custom47 g of dark tan oily substance was obtained with a yield of 89.2%

Sources & evidence

ORD record
ord-90de6bbd9782485097c7b25e872f0876
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

Loading…