Formamide → 6-bromoquinazolin-4-ol

HRID 1187271Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH:12]([NH2:14])=O.O>CN1CCCC1=O>[Br:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:12][NH:14][C:7]2=[O:8]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-bromo-2-aminobenzoic acid (7.9 g, 36.6 mmole) in N-methylpyrrolidinone (20 ml) was added formamide (7.25 ml, 182.5 mmole). The reaction mixture was heated at 150° C. for 7 hours, cooled to room temperature, poured into water (400 ml) and stirred for 15 minutes. The resulting suspension was filtered through a sintered glass funnel to collect the precipitate. The solid was dried under vacuum for 16 hrs to give 7.0 g of a tan solid. The resulting compound was characterized as follows: mass spectrometry: M/Z 226; HPLC: method A, retention time (Rt) 1.51 minutes).

Workup

temperaturecooled to room temperature
filtrationThe resulting suspension was filtered through a sintered glass funnel
customto collect the precipitate
customThe solid was dried under vacuum for 16 hrs

Sources & evidence

ORD record: ord-369c2bb79d62455498433ed395211075
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673929B2

Reaction notes

Loading…