Formamide → HCID 178526462, compound

HRID 1696555Notes

Reaction equation

HRID 1696555 reaction equation
[CH:1]([NH2:3])=O.[N+:4]([C:7]1[CH:8]=[C:9]([NH2:16])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=O)([O-:6])=[O:5]>O>[N+:4]([C:7]1[CH:8]=[C:9]2[C:10]([C:11]([OH:13])=[N:3][CH:1]=[N:16]2)=[CH:14][CH:15]=1)([O-:6])=[O:5]

Participants

4

Reactant 2

HCID 713FormamideHCID 120764-Nitroanthranilic acid

Product 1

HCID 178526462HCID 178526462, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of formamide (7.91 g, 176 mmol) and 4-nitroanthranilic acid (4.00 g, 22.0 mmol) was warmed to 160° C. and stirred for 7 h then cooled to RT and stirred overnight. The mixture was diluted with H2O (30 mL) and stirred overnight. The brown solid was collected by filtration and dried to yield 7-nitroquinazolin-4-ol (3.62 g, 86% yield). 1H NMR (300 MHz, DMSO-d6): 8.38-8.33 (m, 2H), 8.27-8.23 (m, 2H).

Workup

  1. temperaturethen cooled to RT
  2. stirringstirred overnight
  3. stirringstirred overnight
  4. filtrationThe brown solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-de72ae9b7ce2401abfe16cc02654b439
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…