Hydrochloric Acid → HCID 90282004, compound

HRID 1497540Notes

Reaction equation

HRID 1497540 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Li+].[Li+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>CN(C)C=O>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11125Lithium CarbonateHCID 223501916-Hydroxy-1H-indole-2-carboxylic acid

Product 1

HCID 90282004HCID 90282004, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxy-1H-indole-2-carboxylic acid (2.66 g) in N,N-dimethylformamide (25.0 mL) was added lithium carbonate (1.22 g), followed by stirring at room temperature for 10 minutes. Benzyl bromide (2.14 mL) was added thereto, followed by stirring at 100° C. for 2 hours. The reaction mixture was lowered to 60° C., and 1 M hydrochloric acid (40.0 mL) was added thereto, followed by leaving to be cooled and extracting with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), and the crude purified product was washed with cold ethanol (5.00 mL) to obtain benzyl 6-hydroxy-1H-indole-2-carboxylate (1.95 g).

Workup

  1. stirringby stirring at 100° C. for 2 hours
  2. customwas lowered to 60° C.
  3. customby leaving
  4. temperatureto be cooled
  5. extractionextracting with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  10. customthe crude purified product
  11. washwas washed with cold ethanol (5.00 mL)

Sources & evidence

ORD record
ord-e6b52c1c7d864810a10f7188b93d8305
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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