Hydrochloric Acid → HCID 10488443, compound

HRID 581168Notes

Reaction equation

HRID 581168 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]([O:16]C)=[O:15])[NH:10][CH:9]=[CH:8]2)=[O:4].C(O)C.[OH-].[Na+].Cl>O>[NH:10]1[C:11]2[C:7](=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[C:13]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 105137935,6-Dimethoxycarbonylindole

Product 1

HCID 10488443HCID 10488443, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of the dimethyl ester produced in step d (1.14 g, 4.9 mmol) in a 5:1 mixture of ethanol:water (12 ml) was added solid sodium hydroxide (0.49 g, 12.4 mmol). The solution was stirred at a gentle reflux for 3 h. The solution was acidifed on cooling to pH2 with hydrochloric acid and then evaporated. The residue was azeotroped with ethanol and then toluene and dried under vacuum. The residue was then extracted with hot acetone (5×20 ml) and the combined extracts were evaporated to leave the title compound (870 mg).

Workup

  1. temperaturea gentle reflux for 3 h
  2. customevaporated
  3. customThe residue was azeotroped with ethanol
  4. dry with materialtoluene and dried under vacuum
  5. extractionThe residue was then extracted with hot acetone (5×20 ml)
  6. customthe combined extracts were evaporated

Sources & evidence

ORD record
ord-d6d7975f136e47188961638934aa813d
Source dataset
uspto-grants-1999_07
Patent number
US05919829

Reaction notes

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