Dimethyl Sulfate → HCID 86681658, compound

Temperature

60 °C

To a solution of potassium 2-(2-methoxy-2-oxoethyl)-6-nitro-1,3-dioxoisoindolin-5-olate (0.380 g, 1.194 mmol) in DMF (10 ml), dimethyl sulfate (0.324 ml, 3.34 mmol) was added, and the mixture was heated at 60° C. for 6 hours and then stirred at 40° C. overnight. Additional dimethyl sulfate (0.116 ml, 1.194 mmol) was added, and the reaction mixture was heated at 60° C. for 4 hours. The mixture was partitioned between 1N NaHCO3 (150 ml) and diethyl ether (100 ml). The organic phase was washed with 1N NaHCO3 (100 ml), and the combined aqueous layers were extracted with diethyl ether (2×100 ml). The organic layers were mixed, washed twice with brine (2×100 ml) and dried over sodium sulfate; the solvent was removed under vacuum affording methyl 2-(5-methoxy-6-nitro-1,3-dioxoisoindolin-2-yl)acetate (0.225 g, 0.765 mmol, 64% yield). MS/ESI+ 294.9 [MH]+). This product was used without any further purification.

1. temperaturethe reaction mixture was heated at 60° C. for 4 hours
2. customThe mixture was partitioned between 1N NaHCO3 (150 ml) and diethyl ether (100 ml)
3. washThe organic phase was washed with 1N NaHCO3 (100 ml)
4. extractionthe combined aqueous layers were extracted with diethyl ether (2×100 ml)
5. additionThe organic layers were mixed
6. washwashed twice with brine (2×100 ml)
7. dry with materialdried over sodium sulfate
8. customthe solvent was removed under vacuum

ORD record

ord-cd1ec3868d02461ba0354b56c3c2d433

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024027B2