Hydrochloric Acid → HCID 19921669, compound

HRID 1647795Notes

Reaction equation

HRID 1647795 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[NH:7][CH:6]=1.[OH-].[K+].Cl>C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19921679HCID 19921679, compound

Product 1

HCID 19921669HCID 19921669, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(3-hydroxypropyl)-1H-indole-5-carboxylate (5.0 g, 21.46mmol) in 50 mL ethanol was added 30 mL of 15% potassium hydroxide in ethanol. The mixture was heated to reflux for 1 h. The mixture was cooled to 0° C. and acidified with concentrated hydrochloric acid to pH 6. The ethanol was removed in vacuo. The residue was diluted with 250 mL of ethyl acetate and washed with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield 3-(3-hydroxypropyl)-1H-indole-5-carboxylic acid (4.30 g, 92%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe ethanol was removed in vacuo
  4. additionThe residue was diluted with 250 mL of ethyl acetate
  5. washwashed with 50 mL of water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48c227a4f7814d0d83d624d1a7958751
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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