Ethylenediamine → 7-Bromo-3-(nitromethyl)-1,2-dihydronaphthalene

HRID 1036385Notes

Reaction equation

HRID 1036385 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.C(N)CN.[N+:17]([CH3:20])([O-:19])=[O:18]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([CH:8]=[C:7]([CH2:20][N+:17]([O-:19])=[O:18])[CH2:6][CH2:5]2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 27335536-Bromo-2-tetralone

Product 1

HCID 674238767-Bromo-3-(nitromethyl)-1,2-dihydronaphthalene

Conditions

Temperature
75 °C

Procedure

Charged 900 g of 6-bromo-2-tetralone, 1.9 L of nitromethane and 37 g of ethylenediamine in 10 L flask. Heated the mixture liquid to 75° C. in a vessel under N2 for 24 hours to complete the reaction. When the reaction was complete, distilled out the excess nitromethane under reduce pressure. Introduced 200 g of silica gel to the residue with cooling. Hexane (10 L×3) was used to extracted, filtered and the hexane layer combined. On cooling, crystals were formed. About 500 g of 7-bromo-1,2-dihydro-3-(nitromethyl)naphthalene was obtained.

Workup

  1. customthe reaction
  2. distillationdistilled out the excess nitromethane
  3. additionIntroduced 200 g of silica gel to the residue
  4. temperaturewith cooling
  5. extractionto extracted
  6. filtrationfiltered
  7. temperatureOn cooling
  8. customcrystals were formed

Sources & evidence

ORD record
ord-136fb6012c4a4f059b0ddc69339c11cb
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

Loading…