Water → 3-(5'-Nitro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile

HRID 853887Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2].[C:19](#[N:22])[CH:20]=[CH2:21].O>CN(C=O)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:21][CH2:20][C:19]#[N:22])[C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 52 °C

Procedure

At room temperature, to a mixture of 5′-nitrospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one(1.75 g, 6.99 mmol) and benzyltrimethylammonium hydroxide (40% aqueous solution, 0.110 mL, 0.699 mmol, 0.1 mole %) in DMF (31 mL) was added acrylonitrile (0.921 mL, 14.0 mmol, 2 eq) drop-wise. and the mixture was heated at 52° C. for 2 hr. The reaction was cooled to room temperature and poured into H2O (160 mL). The reaction mixture was extracted with Et2O. The combined organic extracts were washed with brine and concentrated. The crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN to give the title compound as a yellow solid (2.15 g, 100% ). NMR (300 Mz, DMSO-d6): consistent

Workup

temperatureThe reaction was cooled to room temperature
extractionThe reaction mixture was extracted with Et2O
washThe combined organic extracts were washed with brine
concentrationconcentrated
customThe crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN

Sources & evidence

ORD record: ord-13df433d10e34e2a9f912a95b69e9fa0
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256198B2

Reaction notes

Loading…