Ammonia → 2-Amino-3-bromo-6,7-dimethylnaphthalene-1,4-dione

HRID 444229Notes

Reaction equation

HRID 444229 reaction equation
[NH3:1].[Br:2][C:3]1[C:4](=[O:17])[C:5]2[C:10]([C:11](=[O:14])[C:12]=1Br)=[CH:9][C:8]([CH3:15])=[C:7]([CH3:16])[CH:6]=2>[N+](C1C=CC=CC=1)([O-])=O>[NH2:1][C:12]1[C:11](=[O:14])[C:10]2[C:5]([C:4](=[O:17])[C:3]=1[Br:2])=[CH:6][C:7]([CH3:16])=[C:8]([CH3:15])[CH:9]=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2463472,3-dibromo-6,7-dimethylnaphthalene-1,4-dione

Product 1

HCID 2463482-Amino-3-bromo-6,7-dimethylnaphthalene-1,4-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Dry ammonia was passed through a refluxing solution of 2,3-dibromo-6,7-dimethyl-1,4-naphthoquinone (10 g; mp 237°-238° C.) in dry nitrobenzene (65 ml) for 30 mins. and the orange solid which separated on cooling was filtered off and washed with light petroleum. After removal of ammonium bromide with water, 6.96 g. (86%) of material of mp 228° C. was obtained. Recrystallisation from glacial acetic acid gave analytically pure material of the same melting point. ν max(mull) 3400, 3300, 1680, 1610, 1585, 1570 cm-1. δ(DMSO) 2.35 (6H,s); 7.35 (2H, exchangeable broad singlet); 7.74 (2H,s). (Found; C, 51.50; H, 3.38; N, 4.79; C12H10BrNO2 requires; C, 51.45; H, 3.60; N, 5.00%).

Workup

  1. customand the orange solid which separated
  2. temperatureon cooling
  3. filtrationwas filtered off
  4. washwashed with light petroleum
  5. customAfter removal of ammonium bromide with water, 6.96 g

Sources & evidence

ORD record
ord-f29bb7a1487d41148457acff8bdf0258
Source dataset
uspto-grants-1981_04
Patent number
US04263309

Reaction notes

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