Lithium hydroxide, monohydrate → 1-(7-Methoxyquinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 1869172Notes

Reaction equation

HRID 1869172 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:9]=1)=[O:7]>O1CCCC1.O>[C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68971128Methyl 1-(7-methoxyquinolin-4-yl)-1H-indole-3-carboxylate

Product 1

HCID 689719301-(7-Methoxyquinolin-4-yl)-1H-indole-3-carboxylic acidYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.504 g (12 mmol) of lithium hydroxide monohydrate and 20 cm3 of water are added to 1.3 g (3.91 mmol) of 3-methoxycarbonyl-1-(7-methoxyquinol-4-yl)-1H-indole dissolved in 20 cm3 of tetrahydrofuran. After stirring at reflux for 20 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 30 cm3 of water (pH=10). The resulting aqueous solution is washed with 50 cm3 of ethyl acetate and adjusted to pH 6 with N hydrochloric acid. The resulting precipitate is filtered off and then it is rinsed with three times 20 cm3 of water and twice 20 cm3 of isopropyl ether and dried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. to give 0.9 g of 3-carboxy-1-(7-methoxyquinol-4-yl)-1H-indole in the form of a white powder. Mass spectrum (EI): m/e 318 (M+•).

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. washThe resulting aqueous solution is washed with 50 cm3 of ethyl acetate
  5. filtrationThe resulting precipitate is filtered off
  6. washit is rinsed with three times 20 cm3 of water and twice 20 cm3 of isopropyl ether
  7. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C.

Sources & evidence

ORD record
ord-11b481765b2d440092c4f2531398a684
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

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