Hydrochloric Acid → HCID 18635755, compound

A solution of (±)-(trans)-2-[bis(4-methoxyphenyl)methyl]-2,3,3a,9a-tetrahydro-5-nitro-1H-[1,4]benzodioxino[2,3-c]pyrrole (1.12 g) in formic acid (10 ml) was heated under reflux with 10M hydrochloric acid (0.5 ml), water (1 ml) and chloroform (5 ml) for 70 minutes. The maroon mixture was cooled and partitioned between chloroform (20 ml) and water (10 ml). The chloroform layer was re-extracted with water (10 ml) and the aqueous solutions were sequentially washed with chloroform (20 ml), combined and evaporated to ca. 2 ml, when crystals formed. These were triturated with warm propan-1-ol (5 ml), cooled to 20° for 1 hour and harvested to give a first crop of the title compound (0.58 g). Concentration of the mother liquor gave a small second crop (0.03 g). Recrystallisation of the first crop from slightly aqueous propan-1-ol gave purer title compound (0.54 g) m.p. ca. 280° (dec.).

1. temperatureThe maroon mixture was cooled
2. custompartitioned between chloroform (20 ml) and water (10 ml)
3. extractionThe chloroform layer was re-extracted with water (10 ml)
4. washthe aqueous solutions were sequentially washed with chloroform (20 ml)
5. customevaporated to ca. 2 ml, when crystals
6. customformed
7. customThese were triturated with warm propan-1-ol (5 ml)
8. temperaturecooled to 20° for 1 hour

ORD record

ord-b5c4dcbf017d4abb86bd841344dceeb5

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880801