Hydrochloric Acid → 6-Carboxy-7-methoxy-4-(indol-5-yloxy)quinoline

HRID 853499Notes

Reaction equation

HRID 853499 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2)=[O:4].[OH-].[Li+].Cl>O1CCCC1>[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 229366056-Methoxycarbonyl-7-methoxy-4-(5-indolyloxy)quinoline

Product 1

HCID 229369786-Carboxy-7-methoxy-4-(indol-5-yloxy)quinolineYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 6-methoxycarbonyl-7-methoxy-4-(indol-5-yloxy)quinoline (400 mg) in tetrahydrofuran (5 ml), a 1.5N aqueous lithium hydroxide solution (2.5 ml) was added and the mixture was stirred at room temperature for 3 hours. The reaction solution was adjusted to pH 4 with IN aqueous hydrochloric acid, and the precipitated crystals were filtered out and washed with ethyl acetate to obtain the title compound (280 mg).

Workup

  1. filtrationthe precipitated crystals were filtered out
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-2a5f5a16dc7148d7944d779bc2e097fc
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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