Sulfuric Acid → 8-(4-Methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 2383251Notes

Reaction equation

HRID 2383251 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][N:11]3[CH:17]=[N:18][CH:19]=[C:10]23)=[CH:5][CH:4]=1.S(=O)(=O)(O)O>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][N:11]3[CH:17]=[N:18][CH:19]=[C:10]23)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 669339248-(4-Methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol

Product 1

HCID 669336998-(4-Methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.50 mmol of 8-(4-methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-ol in 10 ml of ethanol is admixed with 3.5 mmol of concentrated sulphuric acid and 0.70 mmol of 10% Pd/C and the reaction mixture is hydrogenated in an autoclave at 4 bar and 60° C. for 4-8 hours. The reaction mixture is filtered over Hyflo and the filtrate is concentrated. The title compound is used without further purification for the next stage. Rt=5.89 (Gradient I).

Workup

  1. filtrationThe reaction mixture is filtered over Hyflo
  2. concentrationthe filtrate is concentrated
  3. customThe title compound is used without further purification for the next stage

Sources & evidence

ORD record
ord-b686e7e1207144bca4425334611998db
Source dataset
uspto-grants-2012_09
Patent number
US08263615B2

Reaction notes

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