1-[4-(Hydroxymethyl)phenyl]-2-cyanoindole → 1-(4-Formylphenyl)-2-cyanoindole

HRID 1769202Notes

Reaction equation

HRID 1769202 reaction equation
[C:1]([C:3]1[N:4]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)#[N:2]>O1CCCC1.[O-2].[O-2].[Mn+4]>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:3]2[C:1]#[N:2])=[CH:13][CH:14]=1)=[O:19]

Participants

4

Reactant 1

HCID 103546391-[4-(Hydroxymethyl)phenyl]-2-cyanoindole

Product 1

HCID 189468581-(4-Formylphenyl)-2-cyanoindoleYield 68.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (0.0038 mole) of 2-cyano-1-[4-(hydroxymethyl)phenyl]indole was dissolved in 150 ml tetrahydrofuran, 10.0 g of activated manganese dioxide was added, and the mixture stirred at room temperature for 16 hours. The reaction was filtered and the filtrate evaporated to an oil, which was crystallized from a mixture of methyl-t-butyl ether and hexane 1:1 to give 0.63 g (0.0026 mole) of 1-(4-formylphenyl)-2-cyanoindole as an oil.

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated to an oil, which
  3. customwas crystallized from a mixture of methyl-t-butyl ether and hexane 1:1

Sources & evidence

ORD record
ord-ee3e1bbf0a8541ada69614329165e091
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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