Sulfuric Acid → Fadrozole

HRID 568543Notes

Reaction equation

HRID 568543 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-2707bd17809342dda274a849aa3eda60
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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