Ammonia → HCID 21184360, compound

HRID 1385210Notes

Reaction equation

HRID 1385210 reaction equation
[Br:1][C:2]1[C:3](=[O:16])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Br)=[C:8]([O:14][CH3:15])[CH:7]=[CH:6][CH:5]=2.[NH3:17]>O1CCCC1>[NH2:17][C:11]1[C:10](=[O:13])[C:9]2[C:4]([C:3](=[O:16])[C:2]=1[Br:1])=[CH:5][CH:6]=[CH:7][C:8]=2[O:14][CH3:15]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 21184368HCID 21184368, compound

Product 1

HCID 21184360HCID 21184360, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500.0 mg (1.5 mmol) of 2,3-dibromo-1,4-dihydro-1,4-dioxo-5-methoxynaphthalene in 25 mL of tetrahydrofuran, a drop of ammonia is added. The color of the reaction medium turns black. A current of ammonia is passed through the medium for 2 h at 20° C. The raw product obtained after evaporation of the solvent is purified on cake (support: silica; eluant: dichloromethane/heptane, 80/20) to produce 347.3 g of a mixture of 2-amino-3-bromo-1,4-dihydro-1,4-dioxo-5-methoxynaphthalene and 2-amino-3-bromo-1,4-dihydro-1,4-dioxo-8-methoxynaphthalene.

Workup

  1. customThe raw product obtained
  2. customafter evaporation of the solvent
  3. customis purified on cake (support: silica; eluant: dichloromethane/heptane, 80/20)

Sources & evidence

ORD record
ord-f620782cca874ca2846ad9f997a86b62
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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