Formamide → 5-Methyl-4-quinazolone

HRID 900312Notes

Reaction equation

HRID 900312 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4](O)=[O:5].[CH:12]([NH2:14])=O>>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:14][CH:12]=[N:1]2

Participants

3

Reactant 2

HCID 713FormamideHCID 1512106-Methylanthranilic acid

Product 1

HCID 1354187585-Methyl-4-quinazoloneYield 73%

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-6-methylbenzoic acid (5 g, 33 mmol) and formamide (15 ml) was heated in a microwave oven reactor at 180° C. for 30 min. After cooling to room temperature, the solid was collected by filtration, washed with water and dried under vacuum to give 1A (3.89 g, 73%) as a solid. The compound has an analytical HPLC retention time=1.019 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=161+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ce7b3e4724c343bea460d585c7963fb8
Source dataset
uspto-grants-2008_04
Patent number
US07358256B2

Reaction notes

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