Hydrochloric Acid → 6-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 492207Notes

Reaction equation

HRID 492207 reaction equation
O.[OH-].[Li+].O.[F:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:25]([O:27]C)=[O:26])=[CH:11][N:12]2[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:8][CH:7]=1.Cl>O1CCCC1>[C:25]([C:10]1[C:9]2[C:13](=[CH:14][C:6]([F:5])=[CH:7][CH:8]=2)[N:12]([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:11]=1)([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68971643Methyl 6-fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylate

Product 1

HCID 689709316-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.57 g (13.6 mmol) of lithium hydroxide monohydrate and 70 cm3 of water are added at a temperature in the region of 20° C. to 1.45 g (4.53 mmol) of 6-fluoro-3-methoxycarbonyl-1-(quinol-4-yl)-1H-indole dissolved in 70 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 13.6 cm3 of N hydrochloric acid. After filtering off and drying the solid residue at atmospheric pressure at 60° C., 1.35 g of 3-carboxy-6-fluoro-1-(quinol-4-yl)-1H-indole are obtained in the form of a yellow solid melting at 190° 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. customdrying the solid residue at atmospheric pressure at 60° C.

Sources & evidence

ORD record
ord-cf6bee09c0354deb93ae77d6976daf81
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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