Hydrochloric Acid → HCID 89462848, compound

HRID 1473254Notes

Reaction equation

HRID 1473254 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([O:18]C)=[O:17])=[C:8]2[C:20]([O:22]C)=[O:21])=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([OH:18])=[O:17])=[C:8]2[C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 89462967HCID 89462967, compound

Product 1

HCID 89462848HCID 89462848, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

A rbf charged with dimethyl 1-(4-fluorobenzyl)-1H-indole-2,3-dicarboxylate (3.79 g, 11.10 mmol) was treated with a solution of KOH (7.48 g, 133 mmol) in Ethanol (13.88 ml) (0.5 M solution) and heated to reflux (95° C. bath temp). After 18 h, the reaction mixture was cooled to ambient temperature, and acidified to pH 1 with 4M HCl and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to afford 1-(4-fluorobenzyl)-1H-indole-2,3-dicarboxylic acid (3.0 g, 9.58 mmol, 86% yield) as a yellowish solid. LCMS (m/z) ES+=314 (M+1).

Workup

  1. temperatureheated
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e98d88eb99514744be2708b81d4d406b
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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