3-Chloro-2-methylaniline → HCID 23674139, compound

Chlorosulfonic acid (516 μl, 7.77 mmol) in chloroform (5 ml) was added dropwise to a solution of 3-chloro-2-methylaniline (844 μl, 6.98 mmol) and TEA (7.8 ml, 56.54 mmol) in chloroform (20 ml) at 0° C. The mixture was stirred for 90 min, concentrated in vacuo and a solution of NaOH (848 mg, 21.2 mmol) in water (10 ml) was added and the mixture stirred for 30 min at room temperature. The reaction was concentrated in vacuo and azeotroped with toluene. The solid obtained was heated in EtOH (50 ml) at 60° C. for 15 min, concentrated in vacuo and EtOAc (50 ml) added. The resulting solid was collected by filtration and the filtrate allowed to stand at room temperature for 4 h. The crystals formed were filtered, washed with EtOAc, and the solids combined to give the title compound (1.44 g, 84%).

1. concentrationconcentrated in vacuo
2. stirringthe mixture stirred for 30 min at room temperature
3. concentrationThe reaction was concentrated in vacuo
4. customazeotroped with toluene
5. customThe solid obtained
6. concentrationconcentrated in vacuo and EtOAc (50 ml)
7. additionadded
8. filtrationThe resulting solid was collected by filtration
9. waitto stand at room temperature for 4 h
10. customThe crystals formed
11. filtrationwere filtered
12. washwashed with EtOAc

ORD record

ord-4f0520d588f54365ba12aec174e4da4c

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102688B2