Sodium Hydroxide → 7-Aminoindole

HRID 2164659Notes

Reaction equation

HRID 2164659 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[Na+]>[Pd].CO>[NH2:11][C:8]1[CH:9]=[CH:10][CH:2]=[C:3]2[C:7]=1[NH:6][CH:5]=[CH:4]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20405281HCID 20405281, compound

Product 1

HCID 1116347-AminoindoleYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a slurry of 1.96 g. of 4-chloro-7-nitroindole in 100 ml. of methanol containing 400 mg. of sodium hydroxide in a 500-ml. Parr bottle was added 196 mg. of 10% palladium on charcoal. The suspension was shaken for 21/2 hours under an initial hydrogen pressure of 3 atmospheres (absorption ceased after 11/2 hours). The catalyst was removed by filtration and the pale yellow solution was evaporated on a rotary evaporator under reduced pressure. The residue was partitioned between 75 ml. of toluene and 35 ml. of water, and the toluene layer washed with 35 ml. of water. The water phases were then extracted with three 75 ml. portions of chloroform. The toluene and chloroform extracts were evaporated to give 950 mg. and 420 mg. respectively, of greyish crystals. On sublimation on the steambath at 0.08 mm., 567 mg. (43%) of 7-aminoindole having a melting point of 98°-99° was obtained.

Workup

  1. additionParr bottle was added 196 mg
  2. custompressure of 3 atmospheres (absorption ceased after 11/2 hours)
  3. customThe catalyst was removed by filtration
  4. customthe pale yellow solution was evaporated on a rotary evaporator under reduced pressure
  5. customThe residue was partitioned between 75 ml
  6. washof water, and the toluene layer washed with 35 ml
  7. extractionThe water phases were then extracted with three 75 ml
  8. customThe toluene and chloroform extracts were evaporated
  9. customto give 950 mg

Sources & evidence

ORD record
ord-3051ba6e223b40538e5f6f3a1d9da6c8
Source dataset
uspto-grants-1985_03
Patent number
US04506078

Reaction notes

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