Ethyl Acetate → HCID 14370016, compound

Temperature

2 °C

N,N'-carbonyldiimidazole (4.86 g, 0.030 mole) was added portionwise to a stirred, aqueous solution of 6-aminocyclohepta[1,2-c]pyridin-5-one (4.20g, 0.0169 mole) maintained at 2° C. After stirring for 30 minutes, ethyl acetate (~300 ml) was added and the mixture stirred until it reached room temperature. The organic phase was extracted with water (150 ml), washed with brine, and dried (MgSO4). The light brown solid isolated after solvent removal was heated (180° C.) for 35 minutes, cooled to room temperature, then quenched with water (200 ml). The aqueous mixture was stirred for about 12 hours and the brown residue collected by filtration, after washing with ethyl acetate (50 ml), then methylene chloride (50 ml), was recrystallized from aqueous ethanol (50%, ~50 ml) to give 0.29 g of the desired product, m.p. >285° C.

1. stirringthe mixture stirred until it
2. customreached room temperature
3. extractionThe organic phase was extracted with water (150 ml)
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. customThe light brown solid isolated
7. customafter solvent removal
8. temperaturewas heated (180° C.) for 35 minutes
9. temperaturecooled to room temperature
10. customquenched with water (200 ml)
11. stirringThe aqueous mixture was stirred for about 12 hours
12. filtrationthe brown residue collected by filtration
13. washafter washing with ethyl acetate (50 ml)
14. custommethylene chloride (50 ml), was recrystallized from aqueous ethanol (50%, ~50 ml)

ORD record

ord-9c4eac5f96e143429779a6383fa349a3

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04803210