Hydrochloric Acid → methyl 6-hydroxy-1H-indole-2-carboxylate

HRID 1947457Notes

Reaction equation

HRID 1947457 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.Cl.[CH3:15]O>>[CH3:15][O:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([OH:1])[CH:10]=2)=[O:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 223501916-Hydroxy-1H-indole-2-carboxylic acid

Product 1

HCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylateYield 77%

Conditions

Temperature
90 °C

Procedure

To a solution of 6-hydroxy-1H-indole-2-carboxylic acid (5.0 g, 28.2 mmol) in MeOH (250 mL) was added concentrated HCl (3 mL) and the reaction mixture was heated (90° C., 3 h). The reaction mixture was cooled (rt) and concentrated in vacuo. The resulting residue was partitioned between EtOAc (50 mL) and H2O (200 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×200 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (4.2 g, 77%). MS (ESI): mass calcd. for C10H9NO3, 191.1; m/z found, 192.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled (rt)
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was partitioned between EtOAc (50 mL) and H2O (200 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×200 mL)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9def1ec0eeb74636a9f0f9bea0ba2fa3
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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