HCID 14698845, compound → HCID 14698846, compound

HRID 1165380Notes

Reaction equation

HRID 1165380 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][F:20])[N:13]=[N:12]1>C(O)(=O)C.O.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][F:20])[N:13]=[N:12]2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 1

HCID 14698845HCID 14698845, compound

Product 1

HCID 14698846HCID 14698846, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 15.0 g (0.096 mole) of 1-(2-fluoro-4-nitrophenyl)-4-(3-fluoropropyl)-1,4-dihydro-5H-tetrazol-5-one in 200 mL of glacial acetic acid and 10 mL of water, heated at 45° C., was added portionwise 15.0 g (0.27 mole) of iron powder. The reaction mixture was allowed to cool to room temperature and stir for approximately two hours. This mixture was filtered through a pad of Celite filter aid. The filtrate was diluted with 200 mL of water, and the resultant mixture was extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving an oil. This oil was purified by column chromatography on silica gel, eluting with methylene chloride, to yield 12.4 g of 1-(4-amino-2-fluorophenyl)-4-(3-fluoropropyl)-1,4-dihydro-5H- tetrazol-5-one as an oil.

Workup

  1. filtrationThis mixture was filtered through a pad of Celite
  2. filtrationfilter aid
  3. additionThe filtrate was diluted with 200 mL of water
  4. extractionthe resultant mixture was extracted with diethyl ether
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationwas filtered
  8. customThe filtrate was evaporated under reduced pressure
  9. customleaving an oil
  10. customThis oil was purified by column chromatography on silica gel
  11. washeluting with methylene chloride

Sources & evidence

ORD record
ord-87b81818c1084be5a937f7a6c2416090
Source dataset
uspto-grants-1990_03
Patent number
US04909829

Reaction notes

Loading…