Hydrochloric Acid → HCID 54121458, compound

HRID 278443

Reaction equation

HRID 278443 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)=[O:5])C.[Mg].Cl>CO>[CH3:1][O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[NH:7]1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 54121458HCID 54121458, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To 5-methoxy-1H-indole-2-carboxylic acid ethyl ester (5 g, 22.8 mmol) in MeOH (150 ml) was added magnesium turnings (2.2 g, 91.6 mmol, 4eq.) and the mixture vigorously mechanically stirred (10-30° C.) for 2 hr. 4N HCl was added (to pH1-2), then 25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml). The combined extracts were then washed with satd. NaCl solution (50 ml), dried (Na2SO4) filtered and evaporated. The crude green oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:3) to afford the title compound (3.21g, 15.5 mmol, 68%) as a yellow solid Mp. 59-61° C., MS: m/e=207.1 (M+).

Workup

  1. extraction25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml)
  2. washThe combined extracts were then washed with satd
  3. dry with materialNaCl solution (50 ml), dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude green oil was chromatographed over SiO2 (Merck 230-400 mesh)
  7. washeluting with EtOAc-nHexane (1:3)

Sources & evidence

ORD record
ord-86fd5dc6478247c9beb8be490dc96900
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Linked notes

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