Dimethyl-p-toluidine → 6-Bromo-4-chloro-3-methanesulfonyl-2-methyl-quinoline

HRID 13652

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2O.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2[Cl:30]

Participants

Conditions

Temperature: 20 °C

Procedure

6-Bromo-3-methanesulfonyl-2-methyl-quinolin-4-ol (example C.1) (6 g, 19 mmol) and N,N-dimethyl-p-toluidine (5.5 mL, 38 mmol) were dissolved in toluene (60 mL) and heated under argon to reflux. The phosphorous oxychloride (1.9 mL, 20.9 mL) was added and heating at reflux continued for 6.5 h. The product precipitated spontaneously upon cooling to 20° C., the crystals were filtered off and washed with little toluene. One obtained 4.19 g (66%) of light brown crystals. Since the product is somewhat soluble in toluene, the mother liquor was extracted with 3 N HCl (2×), sat. NaCl (2×). The residue was purified by chromatography on silica gel in dichloromethane. One obtained 1.17 g (18%) of additional material. MS: m/z=333/335 (M).

Workup

temperatureheated under argon
temperatureto reflux
temperatureheating
temperatureat reflux
customThe product precipitated spontaneously
filtrationthe crystals were filtered off
washwashed with little toluene
customOne obtained 4.19 g (66%) of light brown crystals
extractionthe mother liquor was extracted with 3 N HCl (2×), sat. NaCl (2×)
customThe residue was purified by chromatography on silica gel in dichloromethane

Sources & evidence

ORD record: ord-85758e9ad35f4e1f90481e2fa98a2d49
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728142B2

Linked notes

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