Methanol → 7-Chloro-6-nitroquinazolin-4(1H)-one

HRID 384757Notes

Reaction equation

HRID 384757 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]([OH:8])=O.C([O-])([O-])OC.C([O-])(=O)C.[NH4+:24].[CH3:25]O>O>[N+:11]([C:10]1[CH:9]=[C:5]2[C:4](=[CH:3][C:2]=1[Cl:1])[N:14]=[CH:25][NH:24][C:6]2=[O:8])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 517165Ammonium AcetateHCID 125353672-Amino-4-chloro-5-nitrobenzoic acidHCID 53629101Methylorthoformate

Product 1

HCID 1356875047-Chloro-6-nitroquinazolin-4(1H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 0.94 g (4.3 mmol) of 4-chloro-5-nitroanthranilic acid, 1.96 g (18.5 mmol) of methyl orthoformate, 1.42 g (18.5 mmol) of ammonium acetate, and 4.0 mL of methanol. The reaction was carried out at 120° C. for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and 40 mL of water was added to the reaction mixture. The resulting aqueous mixture was stirred for 15 minutes and filtered to give 0.88 g (isolated yield: 90%) of 6-nitro-7-chloroquinazolin-4-one as a yellow crystalline product.

Workup

  1. customIn a 10-mL volume stainless steel pressure-resistant vessel were placed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-fbc73cf0d2ee48e8ac6a8793f91794ca
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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