Hydrochloric Acid → HCID 23510098, compound

HRID 352570Notes

Reaction equation

HRID 352570 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14]C)[CH:8]=2)=[O:4].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClCCl.C(OCC)(=O)C>[OH:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([C:3]([OH:4])=[O:2])[N:6]2[CH3:16])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 4456126Methyl 6-methoxy-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 23510098HCID 23510098, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-60 °C

Procedure

To a flask under nitrogen was added 576 mg (2.63 mM) of 6-Methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester and 30 ml dichloromethane. The mixture was cooled to −60° C. in dry ice acetone bath and 16 ml 1M boron tribromide in dichloromethane (16 mM) was added. After stirring 45 minutes at −60° C. the mixture was allowed to warm to room temperature and stirred for 5 hours. The mixture was poured into 200 ml saturated sodium bicarbonate solution and stirred for 30 minutes. Hydrochloric acid was added till acidic, ethyl acetate was added and the mixture filtered through a celite plug to remove insoluble solids. The ethyl acetate layer was separated and the aqueous was extracted two more time with ethyl acetate. The combined ethyl acetate layers were dried over magnesium sulfate, filtered and stripped to give 6-Hydroxy-1-methyl-1H-indole-2-carboxylic acid (M/S, ES-, 190.2 M-H)

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 5 hours
  3. stirringstirred for 30 minutes
  4. additionwas added
  5. filtrationthe mixture filtered through a celite plug
  6. customto remove insoluble solids
  7. customThe ethyl acetate layer was separated
  8. extractionthe aqueous was extracted two more time with ethyl acetate
  9. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-f616d5cc49f34dd0968c2636d29deec7
Source dataset
uspto-grants-2004_06
Patent number
US06747053B2

Reaction notes

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