Hydrochloric Acid → HCID 70980134, compound

HRID 1475463Notes

Reaction equation

HRID 1475463 reaction equation
Cl.C([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[C:7]([CH3:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:6]1)(=O)C.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:22][C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[C:13](=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[NH:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 70981313HCID 70981313, compound

Product 1

HCID 70980134HCID 70980134, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 M aqueous HCl (3 mL) was added to a solution of 1-acetyl-3-methyl-3-phenyl-2,3-dihydro-1H-indole-6-carbonitrile (250 mg, 0.9 mmol) in acetonitrile (10 mL). The solution was stirred at reflux for 1 h and then cooled to room temperature. Saturated aqueous NaHCO3 was then added to the reaction mixture until the pH of the solution reached 8 and the product was then extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound (200 mg) as a light brown gum. MS: [M+H]+=235.

Workup

  1. temperatureat reflux for 1 h
  2. extractionthe product was then extracted with EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0eaf8e199c34c33b1cfd80c9c8b2038
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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