Methane → 5,6-Dihydroxyindole

HRID 1440377Notes

Reaction equation

HRID 1440377 reaction equation
[N+]([C:4]1[CH:9]=[C:8]([O:10]CC2C=CC=CC=2)[C:7]([O:18]CC2C=CC=CC=2)=[CH:6][C:5]=1[CH2:26][C:27]#[N:28])([O-])=O.C.C(O)C>[Pd].O>[OH:18][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][C:8]=1[OH:10])[NH:28][CH:27]=[CH:26]2

Participants

6

Reactant 3

HCID 297MethaneHCID 702EthanolHCID 10904838[4,5-Bis(benzyloxy)-2-nitrophenyl]acetonitrile

Product 1

HCID 1146835,6-Dihydroxyindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The reaction mixture is prepared in an autoclave by adding 0.04 mole (15 g) of 2-nitro-4,5-dibenzyloxyphenylacetonitrile, 1.5 g of palladium at a concentration of 10% on charcoal and 1.5 g of charcoal to 120 ml of ethanol containing 3 ml of water. These are heated to 80° C. for 2 hours, with stirring, under a hydrogen pressure of 4.105Pa. After cooling, the reaction mixture, which is treated in the same manner as previously, produces 5,6-dihydroxyindole an equivalent yield.

Workup

  1. customThe reaction mixture is prepared in an autoclave
  2. temperatureAfter cooling
  3. additionthe reaction mixture, which is treated in the same manner as previously,

Sources & evidence

ORD record
ord-b019b17f92bf4a868470d5ae719198b4
Source dataset
uspto-grants-1996_03
Patent number
US05498746

Reaction notes

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