Chloranil → Bis(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanone

HRID 484994노트

반응식

HRID 484994 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][CH3:25])[CH2:19][CH2:18][CH2:17]4)=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2].C1(Cl)C(=O)C(Cl)=C(Cl)C(=[O:29])C=1Cl>C(O)C>[CH2:24]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([C:13]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6]4)=[O:29])=[CH:23][CH:22]=2)[CH2:17][CH2:18][CH2:19]1)[CH3:25]

참가 물질

4

반응물 2

HCID 8371ChloranilHCID 20271004HCID 20271004, 화합물

생성물 1

HCID 3018962Bis(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanone수율 36.4%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To 400 ml absolute ethanol was added with stirring 16 g (0.0478 mole) bis-(N-ethyl-1,2,3,4-tetrahydro-6-quinolyl)methane, prepared as described in A, and 23.82 g chloranil. The green mixture was heated to reflux for 1 hour, cooled to room temperature over 1 hour and rotary evaporated to dryness. The residue was taken up in methylene chloride and eluted through neutral Woelm Alumina. A red solid remained on the top of the column. The fractions were rotary evaporated to dryness and the oil taken up in ethanol to yield light yellow crystals which were collected by filtration to give 6.06 g, mp 120°-120.5° C. (36.4% yield). An ultraviolet spectrum in ethanol gave a λmax of 382 nm. ε was 40,500.

후처리

  1. customprepared
  2. temperatureThe green mixture was heated
  3. temperatureto reflux for 1 hour
  4. customrotary evaporated to dryness
  5. washeluted through neutral Woelm Alumina
  6. customThe fractions were rotary evaporated to dryness
  7. customto yield light yellow crystals which
  8. filtrationwere collected by filtration
  9. customto give 6.06 g, mp 120°-120.5° C. (36.4% yield)

출처 및 근거

ORD 기록
ord-b2d7bd4eb313443c8384052e5b6b673d
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04535052

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