Methanol → HCID 21931751, compound

HRID 1244044Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[CH:16]=C.C[OH:19]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:14])([CH3:15])[C:10](=[O:13])[N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[CH:16]=[O:19]

Participants

Conditions

Temperature: -70 °C

Procedure

A 65 mg (0.28 mmol) solution of 5-methoxy-1,3,3-trimethyl-6-vinyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one in 16 ml of methylene chloride and 4 ml of methanol was cooled to −70° C. Ozone (via an ozone generator) was bubbled into the solution until a blue color was achieved. The reaction mixture was stirred at −70° C. for 30 minutes and warmed to room temperature. Approximately 0.5 ml of dimethyl sulfide was added and the reaction was evaporated. This residue (0.6 g) was used directly in the next step. 1H NMR (CDCl3) δ 10.20 (s, 1H). Mass spectrum: m/e =235 (p+1).

Workup

customOzone (via an ozone generator) was bubbled into the solution until a blue color
temperaturewarmed to room temperature
additionApproximately 0.5 ml of dimethyl sulfide was added
customthe reaction was evaporated

Sources & evidence

ORD record: ord-3d473d66bdad4a1d9f1c9e2775051e03
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119207B2

Reaction notes

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