(5-methoxy-1H-indol-2-yl)methanol → 5-Methoxy-1H-indole-2-carbaldehyde

HRID 2174524Notes

Reaction equation

HRID 2174524 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2>CCOC(C)=O.O=[Mn]=O>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([CH:2]=[O:1])=[CH:11]2

Participants

4

Reactant 1

HCID 10535294(5-methoxy-1H-indol-2-yl)methanol

Product 1

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeYield 76.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 425 (100 mg, 0.56 mmol) and MnO2 (490 mg, 5.6 mmol) in EtOAc (5 mL) were heated to reflux for 24 h. The mixture was filtered over Celite, and the filtrate was concentrated in vacuo and purified by chromatography (0% to 10% EtOAc/hexanes) to yield a pale-yellow powder (75 mg, 76%): mp 143-144° C. (lit.58 140-141° C.). TLC Rf 0.28 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 9.81 (s, 1H), 9.05 (s, 1H), 7.36-7.34 (d, 1H, J=12 Hz), 7.20-7.19 (m, 1H), 7.12-7.11 (d, 1H, J=6 Hz), 7.09-7.07 (dd, 1H, J1=9 Hz, J2=2.5 Hz), 3.86 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 181.8, 155.0, 136.3, 133.4, 127.7, 119.4, 114.15, 113.36, 102.8, 55.7. Elemental analysis calculated for C10H9NO2: C, 68.56; H, 5.18; N, 8.00. Found: C, 68.42; H, 5.34; N, 7.85.

Workup

  1. temperatureto reflux for 24 h
  2. filtrationThe mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified by chromatography (0% to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d6318bc41ed2484b89d85e79a8c37e44
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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