Sulfuric Acid → 6-(4-Pyridylmethyl)-8-(3-nitrophenyl)quinoline

HRID 2209485노트

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HRID 2209485 반응식
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1.O=[As](O[As](=O)=O)=O.S(=O)(=O)(O)O.[NH4+].[OH-].[CH3:38][CH2:39][CH2:40]CCC>O.C(OCC)(=O)C.OCC(CO)O>[N:10]1[CH:9]=[CH:8][C:7]([CH2:6][C:5]2[CH:13]=[C:14]3[C:2](=[C:3]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=4)[CH:4]=2)[N:1]=[CH:40][CH:39]=[CH:38]3)=[CH:12][CH:11]=1

참가 물질

9

반응물 5

HCID 1118Sulfuric AcidHCID 8058HexaneHCID 14771Arsenic pentoxideHCID 14923Ammonium HydroxideHCID 54509567HCID 54509567, 화합물

생성물 1

HCID 98193566-(4-Pyridylmethyl)-8-(3-nitrophenyl)quinoline

시약·촉매·용매 3

HCID 753Glycerol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

4-[4-Amino-3-(3-nitrophenyl)benzyl]pyridine (600 mg) was combined with glycerol (489 mg) and arsenic pentoxide (325 mg) under nitrogen. The reaction mixture was heated to 100° C. for 30 minutes. Concentrated sulfuric acid (406 mg) was added in a dropwise manner and the reaction mixture was further heated to 150° C. for 2 hours. The reaction was monitored by TLC (9:1, hexane:ethyl acetate) where an aliquot was worked up by adding the product from the reaction to H2O, basifying with NH4OH and extracting with ethyl acetate. When TLC indicated that greater than 90% of the starting material had been converted, the reaction mixture was removed from the heat, ice (approximately 1 gm) was added, and NH4OH was added to basify the mixture. A precipitate was filtered out of the mixture, washed with H2O and air dried. The resulting solid was suspended in hot ethyl acetate and filtered. The filtrate was concentrated and chromatographed by preparative thin-layer chromatography (4:1, hexane:ethyl acetate), the spot with the higher Rf value was isolated yielding 181 mg of 6-(4-pyridylmethyl)-8-(3-nitrophenyl)quinoline as a viscous yellow oil. The product was recrystallized from diethyl ether as a light yellow solid.

후처리

  1. temperaturethe reaction mixture was further heated to 150° C. for 2 hours
  2. additionby adding the product
  3. extractionextracting with ethyl acetate
  4. customthe reaction mixture was removed from the heat, ice (approximately 1 gm)
  5. additionwas added
  6. additionNH4OH was added
  7. filtrationA precipitate was filtered out of the mixture
  8. washwashed with H2O and air
  9. customdried
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated
  12. customchromatographed by preparative thin-layer chromatography (4:1, hexane:ethyl acetate)
  13. customthe spot with the higher Rf value was isolated

출처 및 근거

ORD 기록
ord-e3f9f3c5ab8243209ee7ad7bacd66504
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455252

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