Acetic Acid → Racemic 3-azido-4-oxochroman-7-carbonitrile

HRID 470581Notes

Reaction equation

Br[CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([C:13]#[N:14])=[CH:8][CH:9]=2)[O:4][CH2:3]1.C(O)(=O)C.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([C:13]#[N:14])=[CH:8][CH:9]=2)[O:4][CH2:3]1)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: -15 °C

Procedure

3-Bromo-4-oxochroman-7-carbonitrile Int-2-A (140 mg, 0.55 mmol) was dissolved in DMF (3627 μL) and glacial acetic acid (91.0 μL) was added. The solution was cooled to −15° C. To this solution was added sodium azide (54.2 mg, 0.83 mmol) in water (725 μL) dropwise. After stirring for 2 h at −15° C., the reaction mixture was warmed to room temperature and stirred until all the starting material was consumed. The color of the solution turned dark red. The reaction mixture was diluted by the addition of 50 mL water and extracted by EtOAc twice. The combined organic layers were washed with saturated NaHCO3 solution then brine, dried (MgSO4), and filtered before it was concentrated to give racemic 3-azido-4-oxochroman-7-carbonitrile (110 mg, 0.51 mmol, 92.5% yield): LCMS=237.02 [M+Na]+.

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringstirred until all the starting material
customwas consumed
additionThe reaction mixture was diluted by the addition of 50 mL water
extractionextracted by EtOAc twice
washThe combined organic layers were washed with saturated NaHCO3 solution
dry with materialbrine, dried (MgSO4)
filtrationfiltered before it
concentrationwas concentrated

Sources & evidence

ORD record: ord-14acd335d1e84afc92a3c00c18061198
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629282B2

Reaction notes

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