(5-nitro-1H-indol-2-yl)methanol → 5-Nitro-1H-indole-2-carbaldehyde

HRID 11161Notes

Reaction equation

HRID 11161 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH2:13][OH:14])=[CH:7]2)([O-:3])=[O:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]=[O:14])=[CH:7]2)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 10679279(5-nitro-1H-indol-2-yl)methanol

Product 1

HCID 219808825-Nitro-1H-indole-2-carbaldehydeYield 57.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of crude (5-nitro-1H-indol-2-yl)methanol (3.60 g, 18.7 mmol) in chloroform (200 mL) was heated at 50° C. with manganese dioxide (20 g, 0.23 mol) for 3 h. The reaction mixture was then filtered through Celite and concentrated to give 5-nitro-1H-indole-2-carbaldehyde (904) (2.04 g, 57% through two steps). 1H NMR δ [(CD3)2SO] 12.64 (br, 1H), 9.96 (s, 1H), 8.83 (d, J=2.3 HZ, 1H), 8.18 (dd, J=9.0 Hz, 2.3 Hz, 1H), 7.69 (d, J=0.7 Hz, 1H), 7.62 (d, J=9.0 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-820acf7a65ad4819a1d9f74c3a84cfc8
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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