Sodium Bicarbonate → HCID 86659880, compound

HRID 2360159Notes

Reaction equation

HRID 2360159 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=2)[CH:10]([CH3:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(O)(=O)C.C([O-])(O)=O.[Na+]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]([CH3:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86659879HCID 86659879, compound

Product 1

HCID 86659880HCID 86659880, compoundYield 80.2%

Conditions

Temperature
105 °C

Procedure

To 1-benzyl-5-methoxy-3-methylindoline (78.5 mg, 0.310 mmol) was added a solution of 50% hydrogen bromide-acetic acid solution (0.80 mL) at room temperature. After the reaction mixture was stirred at 105° C. overnight, the reaction mixture was neutralized by saturated NaHCO3 aqueous solution, and the solution was extracted with ethyl acetate. The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20) to obtain the title compound (59.5 mg, 80%).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20)

Sources & evidence

ORD record
ord-ce1187aebc3f4e1baf1de9517e232556
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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