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

HRID 484994Notes

Reaction equation

HRID 484994 reaction equation
[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]

Participants

4

Reactant 2

HCID 8371ChloranilHCID 20271004HCID 20271004, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b2d7bd4eb313443c8384052e5b6b673d
Source dataset
uspto-grants-1985_08
Patent number
US04535052

Reaction notes

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