Hydroxide → HCID 58932562, compound

HRID 853853Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 6′-chlorospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (8.85 g, 36.9 mmol), and benzyltrimethylammonuim hydroxide (40% aqueous solution, 1.46 mL, 3.69 mmol, 0.1 mole % ) in anhydrous DMF was heated to 65° C. Acrylonitrile (4.86 mL, 73.9 mmol, 2 eq) was added drop-wise by syringe under a dry N2 atmosphere. After stirring 65 hr. the reaction was cooled to room temperature and poured into water (750 mL) and extracted with Et2O (3×). The combined organic extracts were dried over Na2SO4 and concentrated. The crude product was purified on Biotage KP silica gel using a step gradient of 100% CH2Cl2 followed by CH2Cl2/CH3OH/NH4OH (99.7/0.2/0.1) to give the title compound as a white solid (7.80 g, 73% yield). Anal: Calc'd for C14H13ClN2O3: C, 57.45; H, 4.48; N, 9.59. Found: C, 56.39; H, 4.35; N, 9.35. NMR (400 MHz, DMSO-d6): consistent. IR: consistent; MS: (EI+) m/z 292 [M+] 1 chlorine pattern observed. m.p.163-164° C.; HRMS: consistent.

Workup

temperaturethe reaction was cooled to room temperature
extractionextracted with Et2O (3×)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated
customThe crude product was purified on Biotage KP silica gel using a step gradient of 100% CH2Cl2

Sources & evidence

ORD record: ord-78924410cce04862a8b9acf646e745c6
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256198B2

Reaction notes

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