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

HRID 477997Notes

Reaction equation

HRID 477997 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 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-987e26f49cb04b2b8762f2306ac73c65
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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