Hydrochloric Acid → 5-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 492211Notes

Reaction equation

HRID 492211 reaction equation
O.[OH-].[Li+].O.[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=1)[CH:10]=[C:9]2[C:25]([O:27]C)=[O:26].Cl>O1CCCC1>[C:25]([C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([F:5])[CH:7]=2)[N:11]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:10]=1)([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68968517Methyl 5-fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylate

Product 1

HCID 689708335-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.63 g (15 mmol) of lithium hydroxide monohydrate and 75 cm3 of water are added at a temperature in the region of 20° C. to 1.6 g (5 mmol) of 5-fluoro-3-methoxycarbonyl-1-(quinol-4-yl)-1H-indole dissolved in 75 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 16 hours, the reaction mixture is concentrated under reduced pressure (2.7 kPa) to give a residue which is taken up with 15 cm3 of N hydrochloric acid. After filtering off and drying the solid residue at atmospheric pressure at a temperature in the region of 60° C., 1.44 g of 3-carboxy-5-fluoro-1-(quinol-4-yl)-1H-indole are obtained in the form of a yellow solid melting at approximately 148° C.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. filtrationAfter filtering off
  4. dry with materialdrying the solid residue at atmospheric pressure at a temperature in the region of 60° C., 1.44 g of 3-carboxy-5-fluoro-1-(quinol-4-yl)-1H-indole

Sources & evidence

ORD record
ord-9c730c52d8de41178ce5dd8304d8968a
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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