Ethanol → Methyl indole-6-carboxylate

HRID 1242125Notes

Reaction equation

HRID 1242125 reaction equation
O1CCCC1.C(O)C.CN(C)/[CH:11]=[CH:12]/[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:23]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:20][O:19][C:17]([C:16]1[CH:15]=[C:14]2[C:13]([CH:12]=[CH:11][NH:23]2)=[CH:22][CH:21]=1)=[O:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Product 1

HCID 639844Methyl indole-6-carboxylateYield 39.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixed solvent of tetrahydrofuran (30 ml), ethanol (30 ml) and water (100 ml), added are methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (10.0 g) and sodium hydrosulfite (104.5 g), and stirred at 70° C. for 1 hours. After this is cooled to room temperature, a saturated saline solution is added thereto. Then, this is extracted with chloroform. The organic layer is dried, and the solvent is evaporated away. The resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1) to obtain 6-methoxycarbonylindole (2.79 g).

Workup

  1. temperatureAfter this is cooled to room temperature
  2. additiona saturated saline solution is added
  3. extractionThen, this is extracted with chloroform
  4. customThe organic layer is dried
  5. customthe solvent is evaporated away
  6. customThe resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-c315ac36537f4e9db6abb6977f887501
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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