Sodium Hydroxide → HCID 20222407, compound

HRID 980300Notes

Reaction equation

HRID 980300 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:16])[CH2:12][N+:13]([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:16])[CH2:12][NH2:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20222400HCID 20222400, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20222407HCID 20222407, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-3-(1-methyl-2-nitroethyl)-1H-indole (7.0 g) in dry tetrahydrofuran (100 ml) was added to a stirred suspension of lithium aluminium hydride (1.88 g) in dry tetrahydrofuran (50 ml) under a stream of nitrogen. The mixture was heated under reflux for 8 h, cooled in an ice bath and 2N sodium hydroxide solution (6 ml) was added cautiously. Filtration of the suspension through Hyflo and evaporation of the filtrate gave an amber oil which was chromatographed on kieselgel 60 eluted with methanol to give the title amine as a yellow gum (3.5 g) T.L.C. silica, methanol/ammonia (79:13) Rf 0.27.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 h
  3. temperaturecooled in an ice bath
  4. filtrationFiltration of the suspension
  5. customthrough Hyflo and evaporation of the filtrate
  6. customgave an amber oil which
  7. customwas chromatographed on kieselgel 60
  8. washeluted with methanol

Sources & evidence

ORD record
ord-0454bee8edb341dfb378a4444f90b209
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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