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

HRID 1677667Notes

Reaction equation

HRID 1677667 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.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.Cl.[O:24]1CCCC1>>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:3]2[C:2]([CH3:12])([CH3:1])[CH2:7][CH2:6][N:5]3[CH:8]=[N:9][C:10]([OH:24])=[C:4]23)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 669337797,7-dimethyl-6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-oneHCID 178491912HCID 178491912, compound

Product 1

HCID 673532618-(4-Methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-ol

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-07245b6867ea408b989edcc07a20a54b
Source dataset
uspto-grants-2011_08
Patent number
US08008334B2

Reaction notes

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