Trisodium Phosphate → 7-methyl-1H-indol-5-ol

HRID 2173904Notes

Reaction equation

HRID 2173904 reaction equation
N(S([O-])(=O)=O)(S([O-])(=O)=O)[O].[K+].[K+].P([O-])([O-])([O-])=[O:14].[Na+].[Na+].[Na+].[CH3:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:30]=1[NH:29][CH2:28][CH2:27]2>CC(C)=O.C(OCC)(=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([OH:14])[CH:25]=[C:26]2[C:30]=1[NH:29][CH:28]=[CH:27]2

Participants

6

Reactant 3

HCID 24243Trisodium PhosphateHCID 3032624Potassium nitrosodisulfonateHCID 123777887-Methyl-2,3-dihydro-1H-indole

Product 1

HCID 189327347-methyl-1H-indol-5-ol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium nitrosodisulfonate (46.1 g, 172 mmol) was added to a 0.1 M aqueous solution of sodium phosphate at pH=7 (1 L) at room temperature. 7-Methylindoline (CAS #: 65673-86-1) (10.4 g, 78 mmol) was dissolved in 100 mL of acetone and added to the reaction in one portion at room temperature. After 30 minutes the reaction was diluted with ethyl acetate and the organic layer was separated. The aqueous layer was then extracted with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated. The resulting residue was absorbed onto silica and then purified by silica gel flash chromatography (0-50% ethyl acetate in heptanes) to provide the title compound. MS (ESI+) m/z 148.08 (M+H).

Workup

  1. additionadded to the reaction in one portion at room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was then extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was absorbed onto silica
  8. custompurified by silica gel flash chromatography (0-50% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-edd056e0e9f24e3497d094fac033db18
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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