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

HRID 1949150

反応式

HRID 1949150 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-86a2f937289f468ba8a929400e90d358
出典データセット
uspto-grants-2013_03
特許番号
US08399673B2

関連ノート

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