Methane → 5,6-Dihydroxyindole

HRID 1721161Notes

Reaction equation

HRID 1721161 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 in 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-f21020e9fa9b4b739ae9fb61b7523e59
Source dataset
uspto-grants-1996_04
Patent number
US05508464

Reaction notes

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