Methanol → HCID 135589780, compound

HRID 384762Notes

Reaction equation

HRID 384762 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([NH2:13])=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:24].[CH3:25]O>>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][C:5]=1[OH:14])[N:13]=[CH:25][NH:24][C:9]2=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 517165Ammonium AcetateHCID 23033002HCID 23033002, compoundHCID 53629101Methylorthoformate

Product 1

HCID 135589780HCID 135589780, compoundYield 55%

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 0.50 g (7.5 mmol) of 5-nitro-4-hydroxyanthranilic acid, 0.80 g (7.5 mmol) of methyl orthoformate, 0.58 g (7.5 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 120° C. for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and methanol was distilled off under reduced pressure. Then, 5 mL of water was added to the reaction mixture. The precipitated crystalline product was collected by filtration and dried under reduced pressure to give 0.29 g (isolated yield: 55%) of 6-nitro-7-hydroxyquinazolin-4-one as a yellow crystalline product.

Workup

  1. customIn a 10-mL volume stainless steel pressure-resistant vessel were placed
  2. distillationmethanol was distilled off under reduced pressure
  3. additionThen, 5 mL of water was added to the reaction mixture
  4. filtrationThe precipitated crystalline product was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-ce049e047d7a46388d14fe3550722182
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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