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

HRID 1516108Notes

Reaction equation

HRID 1516108 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 150 C in a microwave (power: 60 W) 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. customis irradiated at 150 C in a microwave (power: 60 W) until TLC
  2. customcompletion of reaction (20 minutes)
  3. temperatureAfter cooling
  4. washthe reaction mixture is rinsed with ethyl acetate
  5. customevaporated under reduced pressure
  6. customThe crude is purified by flash chromatography (silica gel; ethyl acetate/hexanes)
  7. customto give the above product

Sources & evidence

ORD record
ord-aa8492edfe424a409943f34fe941f6e6
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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