Hydrochloric Acid → 2-Chloroquinoline-6-sulfonyl chloride

Temperature

0 °C

2-Chloroquinolin-6-amine (6.45 g, 36.1 mmol) was dissolved in acetic acid (50 mL) and hydrochloric acid, 37% (14 mL) and cooled to 0° C. A solution of sodium nitrite (2.74 g, 39.7 mmol) in water (8 mL) was then added dropwise, and the reaction mixture was then stirred at 0° C. for 15 min. the entire reaction mixture was then poured into a 0° C. solution of sulfur dioxide, copper(II) chloride and acetic acid (1 L, 36.1 mmol; solution prepared as described for Example 11). The reaction mixture was allowed to warm to room temperature overnight. LC-MS at this time showed reaction had progressed to completion. The reaction mixture was then concentrated, and the residue was partitioned between ethyl acetate and water. The aqueous phase was back extracted, and the combined organic phases were dried over MgSO4, filtered and concentrated to afford a creamy orange solid, which was dried under high vacuum to provide 8.21 g (87% yield) of product.

1. customthe entire reaction mixture
2. temperatureto warm to room temperature overnight
3. customreaction
4. concentrationThe reaction mixture was then concentrated
5. customthe residue was partitioned between ethyl acetate and water
6. extractionThe aqueous phase was back extracted
7. dry with materialthe combined organic phases were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto afford a creamy orange solid, which
11. customwas dried under high vacuum

ORD record

ord-329808aaf2f14a6b9e8afa702cc145d5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697739B2