Hydrochloric Acid → 3-(2-methoxyphenyl)-1H-indazole-5-carbonitrile

HRID 1353725Notes

Reaction equation

HRID 1353725 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=2)[N:11](C2CCCCO2)[N:10]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=2)[NH:11][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 224801423-(2-methoxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile

Product 1

HCID 224800393-(2-methoxyphenyl)-1H-indazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.539 g, 2.17 mmol) was dissolved in 10 mL of tetrahydrofuran. Aqueous hydrogen chloride (10 mL, 6.0N) was added and the reaction mixture was stirred at room temperature for 12 hours, then reflux temperature for 7 hours. The pH of the reaction was neutralized using saturated sodium bicarbonate and the crude was extracted with ethyl acetate (3×15 mL). Attempt to purify the crude by column chromatography was unsuccessful: ES-MS (m/z) 250 [M+1]+.

Workup

  1. temperaturereflux temperature for 7 hours
  2. extractionthe crude was extracted with ethyl acetate (3×15 mL)
  3. customto purify the crude by column chromatography

Sources & evidence

ORD record
ord-fae9ba86d32248309e1ccbefc0d6867b
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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