4-chloro-2-fluoro-5-nitrophenyl-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one → 1-(5-amino-4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

HRID 1608036Notes

Reaction equation

HRID 1608036 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][F:20])[N:13]=[N:12]2)=[C:4]([F:21])[CH:3]=1.[H][H]>[Pt]=O.C(O)C>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:21])=[C:5]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][F:20])[N:13]=[N:12]2)[CH:6]=1

Participants

5

Reactant 2

HCID 145516164-chloro-2-fluoro-5-nitrophenyl-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 145516171-(5-amino-4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-oneYield 246.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a 500 ml Parr hydrogenation bottle was added 0.2 g of platinum oxide, 200 ml of ethanol, then 14.0 g (0.014 mole) of 1-(4-chloro-2-fluoro-5-nitrophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one. The bottle was placed in a Parr hydrogenator and the reaction mixture hydrogenated until the theoretical amount of hydrogen was taken up. The bottle was removed from the hydrogenator and the reaction mixture filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was dissolved in methylene chloride and subjected to column chromatography on silica gel. The appropriate fractions were combined and concentrated under reduced pressure to yield 10.0 g of 1-(5-amino-4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one; m.p. 84°-°86° C. The reaction was repeated several times.

Workup

  1. customThe bottle was removed from the hydrogenator
  2. filtrationthe reaction mixture filtered
  3. concentrationThe filtrate was concentrated under reduced pressure to a residue
  4. dissolutionThe residue was dissolved in methylene chloride
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4e64d6a80784eb7b150fe3e95a20921
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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