N-[2-(Hydroxymethyl)-1H-indol-5-yl]acetamide → 5-Acetamino-2-indolecarboxaldehyde

HRID 1455892Notes

Reaction equation

HRID 1455892 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:14][OH:15])=[CH:8]2)[C:2]([CH3:4])=[O:3]>C(O)C.O=[Mn]=O>[NH:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH:14]=[O:15])=[CH:8]2)[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 1

HCID 10750711N-[2-(Hydroxymethyl)-1H-indol-5-yl]acetamide

Product 1

HCID 107981515-Acetamino-2-indolecarboxaldehydeYield 100%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 15 (100 mg, 0.5 mmol) in ethanol (10 mL) was added MnO2 (250 mg) and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was filtered and the solid was washed with ethanol. The solvent was removed in vacuo and a grey solid 16 was obtained (97 mg, 100% yield). An analytical sample was recrystallized in ethyl acetate. mp: 200° C. (dec). 1H NMR (DMSO-d6, ppm): 11.80 (s, 1 H, NH), 9.84 (s, 1 H, NH), 9.81 (s, 1 H, CHO), 8.09 (s, 1 H, Ar--H), 7.38-7.32 (m, 3 H, Ar--H), 2.04 (s, 3 H, CH3), Anal. (C11H10N2O2 0.4H2O), C, H, N.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with ethanol
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-132d1281042446f3901008f5fe59267b
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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