Ethanol → Ethyl 5-chloroquinoline-6-carboxylate

HRID 581994

반응식

HRID 581994 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 53760849Ethyl 5-chloroquinoline-6-carboxylate수율 32%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
140 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-afc681b4da1548e9aa1fcdc23da459e2
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922734

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