Hydrochloric Acid → HCID 50907649, compound

HRID 1191681Notes

Reaction equation

HRID 1191681 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18]C)=[O:17])[C:7]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:6]2.[OH-].[Na+].Cl>O1CCCC1CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([OH:18])=[O:17])[C:7]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69670931HCID 69670931, compound

Product 1

HCID 50907649HCID 50907649, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-(5-methoxy-2-phenylindol-1-ylmethyl)benzoate (48.6 mg) in tetrahydrofuran-methanol (7/3, 1.1 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.196 mL) at room temperature, and the mixture was stirred at 60° C. for 2 hours. 1 mol/L Hydrochloric acid (10 mL) was added to the reaction mixture at room temperature and this resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (44.7 mg).

Workup

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5b4bb1eb77741e08a1e1766ab4b4846
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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