Lithium Hydroxide → 2-(5-cyano-1H-indol-3-yl)acetic Acid

HRID 1819685Notes

Reaction equation

HRID 1819685 reaction equation
ClC1C=C(C=C(Cl)C=1N)CN.[C:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]([O:26]C)=[O:25])#[N:13].[Li+].[OH-].CCOC(C)=O>C1COCC1.O>[C:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]([OH:26])=[O:25])#[N:13]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 18800597methyl 2-(5-cyano-1H-indol-3-yl)acetateHCID 189757634-Amino-3,5-dichlorobenzylamine

Product 1

HCID 107266882-(5-cyano-1H-indol-3-yl)acetic AcidYield 68.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step H (3): To a solution of methyl 2-(5-cyano-1H-indol-3-yl)acetate (18 mg, 0.08 mmol) in THF (0.8 mL) was added a solution of LiOH (9.6 mg, 0.4 mmol) in water (0.3 mL). The mixture was stirred at rt for 3 h. 50 mL of EtOAc was added, and the resulting solution was washed with 0.1 N HCl and water. The organic layer was dried over Na2SO4, and the solvents was removed to give 11 mg of the title compound 2-(5-cyano-1H-indol-3-yl)acetic acid (yield, 68.7%). MS (ESI) (M−H)+=199.15. 1H NMR (500 MHz, CD3OD) δ ppm 4.86 (s, 2 H) 7.37 (s, 1 H) 7.40 (dd, J=8.24, 1.53 Hz, 1 H) 7.50 (d, J=8.54 Hz, 1 H) 8.01 (s, 1 H).

Workup

  1. washthe resulting solution was washed with 0.1 N HCl and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvents was removed

Sources & evidence

ORD record
ord-2f8929bbed0e458e839e971796043edc
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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