Hydrochloric Acid → HCID 59740492, compound

HRID 220618Notes

Reaction equation

HRID 220618 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:5])C.O[Li].O.Cl>C1COCC1.CCO.O>[Cl:15][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67414308HCID 67414308, compound

Product 1

HCID 59740492HCID 59740492, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 53 mg (0.16 mmol) of 5-chloro-7-morpholin-4-ylmethyl-1H-indole-2-carboxylic acid ethyl ester in THF/EtOH/H2O (2.5 ml) at RT was added 21 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 12 mg (25%) of 5-chloro-7-morpholin-4-ylmethyl-1H-indole-2-carboxylic acid as a white solid. ES-MS m/e (%): 293.1 (M−H+).

Workup

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

Sources & evidence

ORD record
ord-ef6abe8da88345c689baf55674aa05f3
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

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