Ethylenediamine → 3-(Nitromethyl)-1,2-dihydronaphthalene

HRID 1613656Notes

Reaction equation

HRID 1613656 reaction equation
[CH2:1]1[C:10](=O)[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(N)CN.[N+:16]([CH3:19])([O-:18])=[O:17]>>[N+:16]([CH2:19][C:10]1[CH2:1][CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:9]=1)([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 682662-Tetralone

Product 1

HCID 153234983-(Nitromethyl)-1,2-dihydronaphthalene

Procedure

A solution of β-tetralone (Aldrich Chemical Co., Milwaukee, Wis. 53233) (24.5 gm) and ethylenediamine (1.75 gm) in nitromethane (250 ml) was heated at 80° for 16 hours. The reaction mixture was filtered, and the filtrate was evaporated to give a red oil. This was partially purified by elution through a short silica column, eluting with hexane/EtOAc (9:1 v/v). The product was a pink oil (26 gm) which was not purified further but was taken directly for the next reaction.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give a red oil
  4. customThis was partially purified by elution through a short silica column
  5. washeluting with hexane/EtOAc (9:1 v/v)
  6. customwas not purified further
  7. customwas taken directly for the next reaction

Sources & evidence

ORD record
ord-9a68f28ed1c54ca8b16b1ad6187bb904
Source dataset
uspto-grants-1993_03
Patent number
US05194450

Reaction notes

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