Hydrochloric Acid → HCID 86621044, compound

Temperature

0 °C

3-Bromo-2-methyl-benzo[b]thiophene-7-carboxylic acid methyl ester 7.82 g, 27.43 mmol) was treated with NaOH (5 M, 28 mL, 140 mmol) and H2O (100 mL). It is refluxed for 4 h; cooled to 0° C., and acidified to pH (3-4) using 5 M HCl. The resulting precipitate is collected by filtration, washed with H2O (50 mL), and dried in a vac-oven. The material obtained is then treated with oxalyl chloride (2M, 27 mL) with a few drops of DMF. The reaction is stirred at 0° C. for 10 min, and at rt for 4 h. The excess reagent and solvent are removed in vacuo. The residue is finally treated with N,O-dimethyl hydroxylamine hydrochloride (4.00 g, 41.14 mmol) and Et3N (9.6 mL, 68.58 mmol) and CH2Cl2 (200 mL), and the resulting reaction mixture is stirred at rt for 2 h. It is diluted with CH2Cl2 (200 mL), washed with 0.1 M HCl (3×300 mL); dried with Na2SO4, filtered and concentrated. Purification of the crude material by chromatography gives the title compound (6.87 g, 21.89 mmol, 53%). 1H NMR (CDCl3): δ. 2.56 (s, 3H), 3.42 (s, 3H), 3.59 (s, 3H), 7.45 (t, J=7.9 Hz, 2H), 7.81-7.87 (m, 1H) ppm. ES-MS (m/z): calcd for C12H12BrNO2S (M)+: 314.1. found: 314.2.

1. temperatureIt is refluxed for 4 h
2. filtrationThe resulting precipitate is collected by filtration
3. washwashed with H2O (50 mL)
4. customdried in a vac-oven
5. customThe material obtained
6. waitat rt for 4 h
7. customThe excess reagent and solvent are removed in vacuo
8. customthe resulting reaction mixture
9. stirringis stirred at rt for 2 h
10. washwashed with 0.1 M HCl (3×300 mL)
11. dry with materialdried with Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customPurification of the crude material by chromatography

ORD record

ord-5388aa711c3546f08fedb1c902252f1e

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557103B2