Ethanol → Ethyl 5-chloroquinoline-6-carboxylate

HRID 581994

反応式

HRID 581994 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([Cl:13])[CH:3]=1.O[CH2:15][CH:16]([CH2:18]O)O.[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+].C(O)C>S(=O)(=O)(O)O>[Cl:13][C:4]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=[C:2]2[C:3]=1[CH:15]=[CH:16][CH:18]=[N:1]2

参加物

6

反応物 4

HCID 702EthanolHCID 753GlycerolHCID 31389Sodium 3-nitrobenzenesulfonateHCID 13287887Ethyl 4-amino-2-chlorobenzoate

生成物 1

HCID 53760849Ethyl 5-chloroquinoline-6-carboxylate収率 32%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
140 °C

実験手順

A mixture of ethyl 4-amino-2-chlorobenzoate (20 g), glycerol (32.17 g) and sodium 3-nitrobenzenesulfonate (46.73 g) in sulfuric acid (75%) (160 ml) was stirred for 3 hours at 100° C. and for 1 hour at 140° C. After the mixture was cooled to 60° C. and ethanol (200 ml) was added, the mixture was stirred for 16 hours at 60° C. Ethanol was evaporated and the residue was poured into ice water, neutralized with NH4OH and extracted with ethylacetate. The separated organic layer was dried over MgSO4, filtered and the filtrate evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /ethylacetate 97.5/2.5). The desired pure fractions were collected and evaporated, yielding 7.56 g (28%) ethyl 5-chloro-6-quinolinecarboxylate (intermediate 1).

後処理

  1. temperatureAfter the mixture was cooled to 60° C.
  2. stirringthe mixture was stirred for 16 hours at 60° C
  3. customEthanol was evaporated
  4. additionthe residue was poured into ice water
  5. extractionextracted with ethylacetate
  6. dry with materialThe separated organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /ethylacetate 97.5/2.5)
  10. customThe desired pure fractions were collected
  11. customevaporated

出典と根拠

ORDレコード
ord-afc681b4da1548e9aa1fcdc23da459e2
出典データセット
uspto-grants-1999_07
特許番号
US05922734

関連ノート

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