Dimethylformamide → 2-Oxo-2,3-dihydro-benzooxazole-5-carbonitrile

HRID 1846205Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[CH3:12][N:13](C=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:10]=[C:8]1[NH:7][C:6]2[CH:11]=[C:2]([C:12]#[N:13])[CH:3]=[CH:4][C:5]=2[O:9]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-bromo benzoxazolinone (1 g, 4.7 mmol) in DMF (15 mL), were added Zn(CN)2 (1 g, 9.4 mmol) and Pd(PPh3)4. The reaction was stirred at 150° C. for 24 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite® brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.6 (br s, 1H), 7.5 (dd, J=1.8, 8.4 Hz, 1H), 7.3-7.4 (m, 2H).

Workup

filtrationfiltered through Celite® brand
filtrationfilter agent
concentrationThe organic layer was concentrated
custompurified by column chromatography (silica gel, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-a525423adc434942a3282eecd461f213
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952009B2

Reaction notes

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