Sulfuric Acid → Fadrozole

HRID 477989Notes

Reaction equation

HRID 477989 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 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 h 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-8054153e941c41d996c82affd49a84ee
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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