Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)- → HCID 178419049, compound

HRID 1057319Notes

Reaction equation

HRID 1057319 reaction equation
[N:1]([O-])=O.[Na+].[CH3:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=1)=[O:7]>C(O)(=O)C.S(=O)(=O)(O)O>[OH:7][C:6]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)[N:14]=[N:1][CH:5]=1

Participants

5

Reactant 2

HCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 178419049HCID 178419049, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

The starting material, 4-hydroxy-6,7-dimethoxycinnoline was obtained by adding a solution of sodium nitrite (1.9 g, 27 mmol) to a solution of 2-amino-4,5-dimethoxyacetophenone (5 g, 0.025 mol) in acetic acid (90 ml) and sulphuric acid (15 ml) at a rate to maintain the temperature below 20° C. The mixture was heated at 80° C. for 90 minutes. After cooling and concentrating the solution to half its original volume, the residue was poured into ether (800 ml). The solid was collected by filtration and suspended in water (200 ml). After adjusting to pH7 with sodium hydroxide the solid was filtered, washed with water, methanol and methylene chloride to give 4-hydroxy-6,7-dimethoxycinnoline (4.5 g, 87%).

Workup

  1. temperatureto maintain the temperature below 20° C
  2. temperatureAfter cooling
  3. concentrationconcentrating the solution to half its original volume
  4. additionthe residue was poured into ether (800 ml)
  5. filtrationThe solid was collected by filtration
  6. filtrationwas filtered
  7. washwashed with water, methanol and methylene chloride

Sources & evidence

ORD record
ord-2b7e8557ca464d0eae1fb4091de99504
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

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