Sulfuric Acid → Fadrozole

HRID 2290574Notes

Reaction equation

HRID 2290574 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=O.[NH:18]=[N+]=[N-].S(=O)(=O)(O)O>C1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24530Hydrazoic acidHCID 140971985-(p-Formylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Product 1

HCID 59693Fadrozole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2.01 g of 5-p-formylphenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine and 0.96 g of hydrazoic acid in 30 ml of benzene is maintained by external cooling at room temperature, while 0.8 ml of concentrated sulfuric acid is added dropwise. The reaction mixture is stirred for 2 hours and neutralized. The organic phase is separated, dried over sodium sulfate and evaporated to yield an oil which is chromatographed on silica gel with ethyl acetate to yield the title compound.

Workup

  1. additionis added dropwise
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto yield an oil which
  6. customis chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-7a7c0d5715984072bab785ceaf26cb11
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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