Hexane → 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide

HRID 1949150

반응식

HRID 1949150 반응식
[Cl:1][C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCN(CC)CC.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][NH2:28].CCCCCC>S(Cl)(Cl)=O>[Cl:1][C:2]1[C:11]([C:12]([NH:28][CH2:27][C:23]2[S:22][CH:26]=[CH:25][CH:24]=2)=[O:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 8471TriethylamineHCID 34005(2-Thienylmethyl)amineHCID 8471632-Chloroquinoline-3-carboxylic acid

생성물 1

HCID 866453382-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide수율 48%

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

반응 조건

온도
0 °C

실험 절차

A solution of 2.1 g (10.0 mmol) 2-chloroquinoline-3-carboxylic acid in thionyl chloride (60 ml) was heated for 2 h at 85° C. Then excess thionyl chloride was removed under vacuum. The residue was taken up with DCM (60 ml) and the solution was cooled to 0° C. and then mixed with 4.0 ml (30.0 mmol) NEt3 and 1.03 ml (10.0 mmol) thiophene-2-methylamine. After stirring for 90 min at RT it was diluted with EE and washed with a saturated aqueous NH4Cl solution. The aqueous phase was extracted with EE. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) with the residue yielded 1.44 g (4.8 mmol, 48%) 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide.

후처리

  1. customThen excess thionyl chloride was removed under vacuum
  2. additionwas diluted with EE
  3. washwashed with a saturated aqueous NH4Cl solution
  4. extractionThe aqueous phase was extracted with EE
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to small volume under vacuum

출처 및 근거

ORD 기록
ord-86a2f937289f468ba8a929400e90d358
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399673B2

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