Formamide → 6-bromoquinazolin-4-ol

HRID 1272490Notes

Reaction equation

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

Participants

Conditions

Temperature: 180 °C

Procedure

2-Amino-5-Bromo-benzoic acid (10.817 g, 50 mmol) was suspended in 70 ml formamide. The mixture was heated at 180° C. for 7 hrs. The cooled solution was diluted with 100 ml cold water and filtered. The tan solid was washed with di water and used for the next step reaction without further purification. 10.2 g product was obtained. Yield: 90%. 1H NMR (500 MHz, DMSO-d6): δ 7.61430–7.63179(d, J=8.745 Hz, 1H), 7.94922–7.97149 (dd, J1=8.75 Hz, J2=2.385 Hz, 1H), 8.142421(s, 1H), 8.19136–8.19609(d, J=2.365 Hz, 1H); ESI-MS: m/z 225, 227(M++1)

Workup

filtrationfiltered
washThe tan solid was washed with di water
customused for the next step reaction without further purification

Sources & evidence

ORD record: ord-68cbd07dbb9840199c811fb57bc670df
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208493B2

Reaction notes

Loading…