Hydrochloric Acid → 8-(4-Methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol

HRID 2383252Notes

Reaction equation

HRID 2383252 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][N:5]2[CH:8]=[N:9][CH:10]=[C:4]2[C:3]1=[O:11].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.Cl>O1CCCC1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:3]2([OH:11])[C:2]([CH3:12])([CH3:1])[CH2:7][CH2:6][N:5]3[CH:8]=[N:9][CH:10]=[C:4]23)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 669337797,7-dimethyl-6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-oneHCID 178491912HCID 178491912, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7.90 mmol of 7,7-dimethyl-6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one in 50 ml of tetrahydrofuran is admixed at 0-5° C. with 15.8 mmol of 4-methoxyphenylmagnesium bromide (0.5M solution in tetrahydrofuran). The reaction solution is subsequently stirred at 0° C. for 1 hour and then at room temperature for 16 hours. The reaction solution is hydrolysed with 0.5N HCl and extracted with tert-butyl methyl ether. The aqueous phase is rendered basic with saturated aqueous sodium hydrogen carbonate solution and the precipitated solid is isolated by filtration and dried. The title compound is obtained as a grey solid and used without further purification for the next stage. Rt=5.42 (Gradient I).

Workup

  1. waitat room temperature for 16 hours
  2. extractionextracted with tert-butyl methyl ether
  3. customthe precipitated solid is isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-668dfb6fc93640f6a1a40c62c646e675
Source dataset
uspto-grants-2012_09
Patent number
US08263615B2

Reaction notes

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