Methanol → HCID 59129322, compound

HRID 1964305Notes

Reaction equation

HRID 1964305 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=2[C:17]([O-:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[CH3:20]O>[Ni]>[NH2:14][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([C:17]([O:19][CH3:20])=[O:18])[CH:9]=1)[NH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13]2

Participants

4

Reactant 2

HCID 887MethanolHCID 67044111HCID 67044111, compound

Product 1

HCID 59129322HCID 59129322, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 2-tert-butyl-5-nitro-1H-indole-7-carboxylate (2.0 g, 7.2 mmol) and Raney Nickel (200 mg) in CH3OH (50 mL) was stirred for 5 h at the room temperature under H2 atmosphere. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give methyl 5-amino-2-tert-butyl-1H-indole-7-carboxylate (1.2 g, 68%) 1H NMR (CDCl3, 400 MHz) δ 9.34 (brs, 1H), 7.24 (d, J=1.6 Hz, 1H), 7.10 (s, 1H), 6.12 (d, J=1.6 Hz, 1H), 3.88 (s, 3H), 1.45 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off through a celite pad
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-b818fe158e7248e2af03879890a1a2f2
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

Loading…