Sodium Azide → 2-Azido-6,7-dimethylnaphthalene-1,4-dione

HRID 437840Notes

Reaction equation

HRID 437840 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[C:6]1[C:7]([C:9]2[C:14]([C:15](=[O:17])[CH:16]=1)=[CH:13][C:12]([CH3:18])=[C:11]([CH3:19])[CH:10]=2)=[O:8].[N-]=[N+]=[N-]>C(O)C>[N:1]([C:16]1[C:15]([C:14]2[C:9]([C:7](=[O:8])[CH:6]=1)=[CH:10][C:11]([CH3:19])=[C:12]([CH3:18])[CH:13]=2)=[O:17])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 33558AzideHCID 12366402HCID 12366402, compound

Product 1

HCID 123664042-Azido-6,7-dimethylnaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of sodium azide (4.4 g; 0.068 mole) was added at once to a refluxing suspension of 2-bromo-6,7-dimethyl naphtho-1,4-quinone (13.8 g; 0.052 mole) in ethanol (130 ml) and the resulting red solution refluxed for a further 2 mins. After cooling in ice the precipitated azide was separated, washed well with water and recrystallised from ethanol as an orange-red solid, m.p. 116°-119° C. (d).

Workup

  1. temperaturethe resulting red solution refluxed for a further 2 mins
  2. customwas separated
  3. washwashed well with water
  4. customrecrystallised from ethanol as an orange-red solid, m.p. 116°-119° C. (d)

Sources & evidence

ORD record
ord-75b382c7ee28457aad0a78efc70b723a
Source dataset
uspto-grants-1977_06
Patent number
US04032544

Reaction notes

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