Diethylamine → HCID 14372173, compound

To a suspension of furo[2,3-b]pyridine-5-carboxylic acid (3.30 g, 20.2 mmol) in methylene chloride (80 mL), under a nitrogen atmosphere at room temperature, was added oxalyl chloride (4.2 mL, 48 mmol) and then four drops of dimethylformamide. The reaction mixture was stirred until gas evolution ceased (4-5 hours) and a clear solution resulted. This solution was evaporated in vacuo and the excess oxalyl chloride chased by evaporation with benzene. The residue was dissolved in chloroform (50 mL) and diethylamine (5.2 mL, 50 mmol) was added carefully. After 0.5 hours, the chloroform solution was washed with dilute hydrochloric acid, filtered through a pad of charcoal and evaporated to give crude product (5.49 g). This oil was distilled under vacuum to give purified product (3.62 g, 82% yield), bp: 168°-170° C./1.6 mmHg.

1. custom(4-5 hours)
2. customa clear solution resulted
3. customThis solution was evaporated in vacuo
4. customthe excess oxalyl chloride chased by evaporation with benzene
5. dissolutionThe residue was dissolved in chloroform (50 mL)
6. washthe chloroform solution was washed with dilute hydrochloric acid
7. filtrationfiltered through a pad of charcoal
8. customevaporated

ORD record

ord-fc6eda01c23148029ba41eacf5c7f6bd

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808595