7-Nitroindole → 7-Aminoindole

HRID 13697

Reaction equation

HRID 13697 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-])=O>[Pd]>[NH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[NH2:1])[CH:9]=[CH:10]1

Participants

3

Reactant 1

HCID 233967-Nitroindole

Product 1

HCID 1116347-AminoindoleYield 96.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Charge a 3-gal autoclave with 7-nitroindole (250 g, 1.542 moles), 2B-3 ethyl alcohol (5.0 L), and 10% Pd/C (50.0 g). Stir at 50 psi H2 for 2 h at <27° C. When the reaction is deemed complete, filter the reactor contents through Celite followed by concentration of the filtrate to dryness to yield 197.0 g (96.7%) of the title compound as purple solid. 1H-NMR(CD3OD, 300 MHz), δ 7.16 (d, 1H), 7.00 (dd, 1H), 6.81 (t, 1H), 6.50 (dd, 1H), 6.37 (d, 1H).

Workup

  1. filtrationfilter the reactor contents through Celite

Sources & evidence

ORD record
ord-2b65a1f6cbca443e93aec527e743b57a
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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