Potassium Hydroxide → (1-Benzyl-5-phenyl-1H-indol-3-yl)(oxo)acetic Acid

HRID 2221241Notes

Reaction equation

HRID 2221241 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:23](=[O:29])[C:24]([O:26]CC)=[O:25])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)[C:10]([C:23](=[O:29])[C:24]([OH:26])=[O:25])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22032978ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate

Product 1

HCID 10291732(1-Benzyl-5-phenyl-1H-indol-3-yl)(oxo)acetic AcidYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

{1-Benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate (0.680 g, 1.77 mmol), and potassium hydroxide (0.322 g, 5.74 mmol) in THF (10 mL) and water (10 mL), following the procedure described in Step 4 of Example 5. Crystallization from acetonitrile, and drying for 3.5 hours at 70° C., yielded the title compound as a yellow solid (0.392 g, 62%), mp: 193-195° C. (dec.). Mass spectrum (+ES, [M+H]+) m/z 356; 1HNMR (500 MHz, DMSO-d6): δ 13.7-14.2 (br s, 1H), 8.7 (s, 1H), 8.45 (d, 1H, J=0.61 Hz), 7.65 (m, 3H), 7.55 (dd, 1H, J=8.7 Hz and 1.1 Hz), 7.45 (t, 2H, J=7.6 Hz), 7.25-7.35 (m, 6H), and 5.65 ppm (s, 2H). Elemental Analysis for C23H17NO3: Calculated: C, 77.73; H, 4.82; N, 3.94. Found: C, 77.52; H, 4.81; N, 3.95.

Workup

  1. customCrystallization from acetonitrile
  2. customdrying for 3.5 hours at 70° C.

Sources & evidence

ORD record
ord-d7c588a6ca83453ebe51913dd22d4759
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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