Hydrochloric Acid → Fadrozole

HRID 22567Notes

Reaction equation

HRID 22567 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[C:15](C(OCC)=O)=[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 199304305-(p-Cyanophenyl)-3-ethoxycarbonyl5,6,7,8-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)-3-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. The solution is warmed to reflux and 5 ml of 1N hydrochloric acid is added. After 1 h the reaction mixture is 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 5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, m.p. 128°-131°.

Workup

  1. temperatureThe solution is warmed
  2. temperatureto reflux
  3. temperatureAfter 1 h the reaction mixture is cooled
  4. customevaporated
  5. customThe residue is partitioned between water and ethyl acetate
  6. customThe organic layer is separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-a69c0829ded140078ba53794e4f74e80
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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