Potassium Hydroxide → (1-Benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetic Acid

HRID 2221238Notes

Reaction equation

HRID 2221238 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[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 86588621Ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetate

Product 1

HCID 10108853(1-Benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetic AcidYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(1-Benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetic acid was prepared from ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetate (1.90 g, 4.96 mmol), and potassium hydroxide (0.856 g, 15.3 mmol) in THF (20 mL) and water (20 mL), following the procedure described in Step 4 of Example 5. Crystallization from acetonitrile and drying for 8 hours at 70° C. yielded the title compound as a light yellow solid (1.23 g, 70%), mp: 210-212° C. (dec.). Mass spectrum (+ES, [M+H]+) m/z 356; 1HNMR (500 MHz, DMSO-d6): δ 13.8-14.2 (br s, 1H), 8.7 (s, 1H), 8.25 (d, 1H, J=8.2 Hz), 7.9 (s, 1H), 7.65 (d, 2H, J=8.1 Hz), 7.6 (d, 1H, J=8.4 Hz), 7.45 (t, 2H, J=7.7 Hz), 7.3-7.35 (m, 5H), 7.25-7.3 (m, 1H), and 5.65 ppm (s, 2H). Elemental Analysis for C23H17NO3: Calculated: C, 77.73; H, 4.82; N, 3.94. Found: C, 77.58; H, 4.68; N, 3.90.

Workup

  1. customCrystallization from acetonitrile
  2. customdrying for 8 hours at 70° C.

Sources & evidence

ORD record
ord-0a3e1f01391c45758e6d34d2f1f2c4f8
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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