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Sodium Chlorite → 2-Chloro-5-methoxy-1-phenyl-1h-indole-3-carboxylic acid

HRID 1510080
Notes
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Reaction equation

HRID 1510080 reaction equation
[Cl:1][C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([O:13][CH3:14])=[CH:6][CH:5]=2.Cl([O-])=[O:22].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.CC(=CC)C.O>[Cl:1][C:2]1[N:3]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:4]2[C:9]([C:10]=1[C:11]([OH:22])=[O:12])=[CH:8][C:7]([O:13][CH3:14])=[CH:6][CH:5]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 872052842-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

Product 1

HCID 669204422-Chloro-5-methoxy-1-phenyl-1h-indole-3-carboxylic acidYield 125.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×
HCID 6386
tert-Butanol
Solvent
HCID 105532-Methyl-2-buteneSolvent

Conditions

Temperature
80 °C

Procedure

The compound of step 3 (456 mg, 1.59 mmol) was dissolved in tert-butanol (15 ml) and 2-methyl-2-butene (3 ml), and a solution of sodium chlorite (1.32 g, 14.6 mmol) and sodium dihydrogenphosphate (1.32 g, 11.0 mmol) in water (6 ml) was added. The reaction mixture was stirred at room temperature for 48 h and afterwards at 80° C. for 2.5 h. The mixture was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to give 602 mg of the crude title compound.

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-353e6e89576140e1ba0c3e512d837320
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08211885B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes