Tetrahydrofuran → HCID 20140105, compound

A mixture of 1.72 g of 4-chloroanthranilic acid, 1.62 g of N,N'-carbonyldiimidazole and 25 ml of tetrahydrofuran was stirred for 3 hours at 5°-25° C. and 1.50 g of 4-(3-pyridinyl)butylamine was added. The mixture was stirred overnight at room temperature, heated at reflux temperature for 1 hour and then with 10 ml of water for 30 minutes. The reaction mixture was concentrated and 100 ml of methylene chloride and 5 ml of 1N sodium hydroxide were added. The layers were separated and the organic layer was concentrated, washed with water, dried over magnesium sulfate and concentrated. The residue was treated with ethanolic hydrogen chloride. The mixture was again concentrated and triturated with acetone to obtain crystals of the desired product, mp 208°-210° C. after recrystallization from ethanol.

1. stirringThe mixture was stirred overnight at room temperature
2. temperatureheated
3. temperatureat reflux temperature for 1 hour
4. concentrationThe reaction mixture was concentrated
5. addition100 ml of methylene chloride and 5 ml of 1N sodium hydroxide were added
6. customThe layers were separated
7. concentrationthe organic layer was concentrated
8. washwashed with water
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated
11. additionThe residue was treated with ethanolic hydrogen chloride
12. concentrationThe mixture was again concentrated
13. customtriturated with acetone

ORD record

ord-567b45f7910c41ff8e4cc5ce0bc478c7

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04743610