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

HRID 13652

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HRID 13652 반응식
[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]

참가 물질

5

반응물 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 178432088HCID 178432088, 화합물

생성물 1

HCID 120016236-Bromo-4-chloro-3-methanesulfonyl-2-methyl-quinoline수율 18%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
20 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-85758e9ad35f4e1f90481e2fa98a2d49
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728142B2

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