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

HRID 1010359
Notes
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Reaction equation

HRID 1010359 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1N 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-33179c6933b54d13a2d50b839a1b74b9
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07973160B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes