Hydrochloric Acid → HCID 3595778, compound

HRID 1058944Notes

Reaction equation

HRID 1058944 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:7]2[CH2:19][C:20]([O:22]CC)=[O:21].Cl>CO>[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:7]2[CH2:19][C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53870927HCID 53870927, compound

Product 1

HCID 3595778HCID 3595778, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (4M, 75 mL) was added to ethyl 5-methyl-2-phenyl-1H-indole-3-acetate (Description 5, 1.61 g) in methanol (150 mL) and the mixture was stirred at room temperature for 2 h. The mixture was cooled to 0° C. , the pH was adjusted to 3.0 with hydrochloric acid (2M) and the mixture was extracted with ethyl acetate. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was recrystallized from ether to give the title compound as a colourless solid (1.1 g, 76%). 1H NMR (360 MHz, CDCl3) δ2.47 (3H, s), 3.85 (3H, s), 7.05 (1H, dd, J 8.3, 1.4 Hz), 7.27 (1H, d, J 11.2 Hz), 7.36-7.49 (4H, m), 7.62 (1H, d, J 9.2 Hz), and 8.05 (1H, br s). m/z (ES+) 266 (M+1).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-594d1d815a024cd8b2ce70d256955d43
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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