Acetic Acid → HCID 118071533, compound

HRID 1775427Notes

Reaction equation

HRID 1775427 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]2/[CH:17]=[CH:18]/[N+:19]([O-:21])=[O:20].C(O)C.[BH4-].[Na+].C(O)(=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]2[CH2:17][CH2:18][N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 12236626HCID 12236626, compound

Product 1

HCID 118071533HCID 118071533, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 5-methoxy-3-[(E)-2-nitrovinyl]-1H-indole-2-carboxylate (4.92 g) and ethanol (100 mL) was added sodium borohydride (1.92 g), followed by stirring at room temperature for 2 hours. To the mixture were added acetic acid and then water under ice-cooling, and the precipitated solid was collected by filtration and dried to obtain ethyl 5-methoxy-3-(2-nitroethyl)-1H-indole-2-carboxylate (4.01 g) as a yellow solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-3bda095e44734634821d47711edb7d37
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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