Nitric Acid → 6-Bromo-2-methoxy-1-nitronaphthalene

HRID 861516Notes

Reaction equation

HRID 861516 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([O:16][CH3:17])[CH:10]=[CH:9]2>C(O)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([N+:1]([O-:4])=[O:2])=[C:11]([O:16][CH3:17])[CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 220971876-Bromo-2-methoxy-1-nitronaphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

10 ml of 98% strength nitric acid dissolved in 70 ml of acetic acid were added dropwise to 50 g (0.21 mol) of 6-bromo-2-methoxynaphthalene dissolved in 350 ml of acetic acid at room temperature. The mixture was heated to 50° C. and, after the product had crystallized, cooled. The precipitate was filtered off with suction to yield 53.1 g (90%) of the product. Melting point 156°-157° C.

Workup

  1. customafter the product had crystallized
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-c67da7286795475fa5870991d3593d3c
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

Loading…