Hydrochloric Acid → 3-Chloro-1H-indole-2-carboxylic acid

HRID 453870Notes

Reaction equation

HRID 453870 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13]CC)=[O:12].O[Li].O.Cl>C1COCC1.CO.O.O>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 13329562ethyl 3-chloro-1H-indole-2-carboxylate

Product 1

HCID 152903193-Chloro-1H-indole-2-carboxylic acidYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

Ethyl 3-chloro-1H-indole-2-carboxylate (19.28 mmol, 1.0 equiv.) was dissolved in THF-MeOH—H2O (2:1:1; 85 ml); LiOH.H2O (57.84 mmol, 3.0 equiv.) was added at 0° C. and the mixture was stirred for 12 h at 25° C. The solvent was reduced under reduced pressure, and the residue was taken up in water (50 ml), adjusted to pH 3 with 1 M HCl and extracted with ethyl acetate (2×100 ml). The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure, and then the product was crystallized with hexane. Yield: 82%

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customthe product was crystallized with hexane

Sources & evidence

ORD record
ord-b7377bdb5e90455587787a9da090b835
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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