Hydrochloric Acid → Fadrozole

HRID 2290576Notes

Reaction equation

HRID 2290576 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 hours at room temperature and 5 ml of 1N hydrochloric acid is added. The reaction mixture is refluxed for 1 hour, 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 hour
  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-3d6d19be58404e1783f31c0ca03094c9
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

Loading…