Ammonium Hydroxide → HCID 178486918, compound

HRID 1154557Notes

Reaction equation

HRID 1154557 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:17]([O-])=O)=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=[O:15])[N:7]=[C:6]2[CH3:16].[OH-].[NH4+]>O>[CH3:1][O:2][C:3]1[C:4]([NH2:17])=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=[O:15])[N:7]=[C:6]2[CH3:16]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178486919HCID 178486919, compound

Product 1

HCID 178486918HCID 178486918, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 13 equivalents of FeSO4.7H2O in water (6 parts) is heated to 95° C. A slurry of 1 equivalent of 6,7-dimethoxy-5-nitro-4-methyl-2(1H)quinazolinone in water (800 ml) at 80° C. is added and the resulting yellow mixture is heated at 98°-100° C. for 15 minutes. Ammonium hydroxide (13 eq) is added to the mixture dropwise over a 15 minute period, maintaining the temperature at 98°-100° C. The resulting black reaction mixture is stirred at 98°-100° C. for 30 minutes, the hot mixture is filtered and the insoluble black residue is washed with hot water. The brownish filtrate is extracted with chloroform. The solvent is removed in vacuo to give a dark brown semisolid crude product, which is chromatographed on a silica gel column. Recrystallization of the crude product from ethyl alcohol affords purified product.

Workup

  1. temperaturethe resulting yellow mixture is heated at 98°-100° C. for 15 minutes
  2. temperaturemaintaining the temperature at 98°-100° C
  3. filtrationthe hot mixture is filtered
  4. washthe insoluble black residue is washed with hot water
  5. extractionThe brownish filtrate is extracted with chloroform
  6. customThe solvent is removed in vacuo
  7. customto give a dark brown semisolid crude product, which
  8. customis chromatographed on a silica gel column
  9. customRecrystallization of the crude product from ethyl alcohol
  10. customaffords
  11. custompurified product

Sources & evidence

ORD record
ord-46ff0047393f44be8bdb90222e5c5f40
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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