Formamide → 6-Nitro-3,4-dihydroquinazolin-4-one

HRID 1751885Notes

Reaction equation

HRID 1751885 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:14]([NH2:16])=O>>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:13]=[CH:14][NH:16][C:9]2=[O:11])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 713FormamideHCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 1353985026-Nitro-3,4-dihydroquinazolin-4-one

Procedure

A mixture of 5-nitroanthranilic acid (2 g, 14.6 mmol) and formamide (2.9 ml, 72 mmol) is irradiated at 15° C. in a microwave (power: 60W) until TLC shows completion of reaction (20 minutes). After cooling, the reaction mixture is rinsed with ethyl acetate and evaporated under reduced pressure. The crude is purified by flash chromatography (silica gel; ethyl acetate/hexanes) to give the above product.

Workup

  1. customcompletion of reaction (20 minutes)
  2. temperatureAfter cooling
  3. washthe reaction mixture is rinsed with ethyl acetate
  4. customevaporated under reduced pressure
  5. customThe crude is purified by flash chromatography (silica gel; ethyl acetate/hexanes)
  6. customto give the above product

Sources & evidence

ORD record
ord-3158ae409cec4795ac3ba5d52ca96e49
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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