(5-nitro-1H-indol-2-yl)methanol → HCID 10702137, compound

HRID 1455890Notes

Reaction equation

HRID 1455890 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([N+:12]([O-])=O)=[CH:7][CH:6]=2>CO.[Pd]>[NH2:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([CH2:2][OH:1])=[CH:11]2

Participants

4

Reactant 1

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

Product 1

HCID 10702137HCID 10702137, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 13 (862 mg, 4.49 mmol) in methanol (50 mL) was added 5% Pd/C (50 mg) and the reaction mixture was hydrogenated for 1 h at a pressure of 50 lb/inch2. The reaction mixture was filtered through celite and the celite was washed with methanol. The solvent was removed in vacuo and 707 mg (97% yield) of grey powder 14 was obtained. mp: 159°-160° C. 1H NMR (DMSO-d6, ppm): 10.44 (s, 1 H, NH), 7.01-6.99 (d, 1 H, J=8.5 Hz, Ar--H), 6.60 (d, 1 H, J=2.0 Hz, Ar--H), 6.43-6.40 (dd, 1 H, J=2.4, 8.5 Hz, Ar--H), 5.97 (brs, 1 H, Ar--H), 5.07 (brs, 1 H, OH), 4.50 (brs, 2 H, CH2OH), 4.30 (brs, 2 H, NH2), Anal. (C9H10N2O), C, H, N.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with methanol
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aa3c202210b14557a6afa99c0215f758
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

Loading…