5-(p-Aminophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine → Fadrozole

HRID 22558

Reaction equation

HRID 22558 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[Cu][C:22]#[N:23]>Cl.O>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:23]

Participants

6

Reactant 3

HCID 152947205-(p-Aminophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridineHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 59693Fadrozole

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of 2.13 g of 5-(p-aminophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 4 ml of concentrated hydrochloric acid and 10 ml of water is cooled in an ice-bath and a solution of 0.78 g of sodium nitrite in 2 ml of water is added slowly. The solution is added via dropping funnel to an ice cooled solution of 3.0 g of copper(I) cyanide in 10 ml of water, keeping the temperature between 30°-40°. The reaction mixture is heated on a steam bath for 1 h, cooled and brought to pH 9. The organic extracts are dried over sodium sulfate and evaporated and the residue is chromatographed on silica gel with ethyl acetate to yield the title compound.

Workup

  1. additionThe solution is added
  2. custombetween 30°-40°
  3. temperatureThe reaction mixture is heated on a steam bath for 1 h
  4. temperaturecooled
  5. dry with materialThe organic extracts are dried over sodium sulfate
  6. customevaporated
  7. customthe residue is chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-14e5b909f4a74155a7d9cebed6739509
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Linked notes

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