Hydrochloric Acid → HCID 59740491, compound

HRID 912753Notes

Reaction equation

HRID 912753 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:15][C:16]#[N:17])=[O:5])C.O[Li].O.Cl>C1COCC1.CCO.O>[C:16]([CH2:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)#[N:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 15272827HCID 15272827, compound

Product 1

HCID 59740491HCID 59740491, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 100 mg (0.46 mmol) of 7-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester (the preparation of which is described in Chem. Pharm. Bull. 1996, 44, 55) in THF/EtOH/H2O (5 ml) at RT was added 50 mg of LiOH.H2O. The reaction mixture was stirred at 45° C. for one hour and then acidified with aqueous HCl 1M. The product was extracted with EtOAc and concentrated under vacuo to afford 80 mg (85%) of 7-Cyanomethyl-1H-indole-2-carboxylic acid as a white solid. ES-MS m/e (%): 199.6(M−H+).

Workup

  1. extractionThe product was extracted with EtOAc
  2. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-7d1ac218ac214a3e9cdf9bab439ce781
Source dataset
uspto-grants-2011_09
Patent number
US08026259B2

Reaction notes

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