Hydrochloric Acid → 5-(2-Nitroethyl)-1H-indole

HRID 128972Notes

Reaction equation

HRID 128972 reaction equation
[BH4-].[Na+].[OH-].[Na+].[N+:5]([CH:8]=[CH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)([O-:7])=[O:6].Cl>C(#N)C.O>[N+:5]([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 544650165-(2-nitro-vinyl)-1H-indole

Product 1

HCID 131097235-(2-Nitroethyl)-1H-indoleYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium borohydride (2.0 g) and 40% w/v aqu. NaOH was added dropwise to a solution of the the product from step (b) (1.9 g) in acetonitrile (55 ml) at 0° C. The pH was maintained at 3-6 by periodic additions of 2N aqu. HCl. The resulting solution was stirred at 0° C. for 2 hours, then diluted with water and extracted with DCM. The combined extracts were washed with brine, dried and evaporated in vacuo to give a yellow oil which was eluted through a silica column using chloroform as eluant to give the desired product as a pale yellow oil (0.78 g).

Workup

  1. temperatureThe pH was maintained at 3-6 by periodic additions of 2N aqu
  2. extractionextracted with DCM
  3. washThe combined extracts were washed with brine
  4. customdried
  5. customevaporated in vacuo
  6. customto give a yellow oil which
  7. washwas eluted through a silica column

Sources & evidence

ORD record
ord-4a527876fe97424dabbbd777c642af79
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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