(+-)-1-Aminoindan → N-(Indan-1-yl)-4-nitro-3-pyridinamine-1-oxide

HRID 1073501Notes

Reaction equation

HRID 1073501 reaction equation
F[C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:12]1([NH2:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>C(O)C>[CH:12]1([NH:21][C:2]2[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 123445(+-)-1-AminoindanHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olate

Product 1

HCID 15053110N-(Indan-1-yl)-4-nitro-3-pyridinamine-1-oxideYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-fluoro-4-nitropyridine-1-oxide (5.6 g) and indan-1-amine (6 g) in 100 ml ethanol was stirred at reflux for one hour and thereafter cooled and concentrated to 12 g of solid. This solid was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane) to give 9.2 g solid, m.p. 137°-138°. An analytical sample was obtained by recrystallizing 2.7 g from ethanol to give 2.5 g crystals, m.p. 141°-142°.

Workup

  1. temperatureat reflux for one hour
  2. temperaturecooled
  3. concentrationconcentrated to 12 g of solid
  4. customThis solid was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-760e47f4fd9e4dd9a040aac84bc7f329
Source dataset
uspto-grants-1990_11
Patent number
US04970219

Reaction notes

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