Hydrochloric Acid → HCID 59442717, compound

HRID 1746158Notes

Reaction equation

HRID 1746158 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=2)[CH2:3][CH2:2]1.[Sn](Cl)Cl.Cl>C(O)C>[CH:1]1([C:4]2[CH:9]=[C:8]([NH2:10])[CH:7]=[C:6]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 594427125-(3-Cyclopropyl-5-nitrophenyl)-1-methyl-1H-tetrazole

Product 1

HCID 59442717HCID 59442717, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3-Cyclopropyl-5-nitrophenyl)-1-methyl-1H-tetrazole (1.4 g, 5.7 mmol) was treated with tin (II) chloride (4.3 g, 22.8 mmol) and hydrochloric acid (0.5 mL) in ethanol (15 mL) at reflux for 1 hour. The solvent was removed under vacuum. The residue was partitioned between ethyl acetate and water. The organic layer was washed with 1M aqueous potassium carbonate solution, dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography, on silica gel, eluting with hexanes:ethyl acetate (70:30), to yield 3-cyclopropyl-5-(1-methyl-1H-tetrazol-5-yl)benzenamine (520 mg, 43% yield) as an off-white solid.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe solvent was removed under vacuum
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 1M aqueous potassium carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography, on silica gel
  8. washeluting with hexanes:ethyl acetate (70:30)

Sources & evidence

ORD record
ord-7657d67200704100aa0ceaa53773b6cc
Source dataset
uspto-grants-2015_10
Patent number
US09149475B2

Reaction notes

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