Hydrochloric Acid → Fadrozole

HRID 477993Notes

Reaction equation

HRID 477993 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2(C(OCC)=O)[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:2].[OH-].[Na+].Cl>CO>[C:1]([C:3]1[CH:4]=[CH:5][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:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 152947195-(p-Cyanophenyl)-5-ethoxycarbonyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Product 1

HCID 59693Fadrozole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.65 g of 5-(p-cyanophenyl)-5-ethoxycarbonyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 10 ml of methanol containing 0.2 g of sodium hydroxide is stirred for 3 h at room temperature and 5 ml of 1N hydrochloric acid is added. The reaction mixture is refluxed for 1 h, cooled and evaporated. The residue is partitioned between water and ethyl acetate. The organic layer is separated, dried over sodium sulfate and evaporated to yield the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 h
  2. temperaturecooled
  3. customevaporated
  4. customThe residue is partitioned between water and ethyl acetate
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-866ee74a0d3d4102bb347605d5c54ada
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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