HCID 18365552, compound → HCID 18365546, compound

HRID 380653Notes

Reaction equation

HRID 380653 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[C:14](=[N:23]O)[CH:13]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:25]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH3:39])([CH3:38])[C:30]1=[CH2:40])[CH:26]([CH3:28])[CH3:27]>C(O)C>[CH2:25]([N:29]1[C:30]2([O:22][C:15]3[C:16]4[C:21]([C:12]([C:9]5[CH:10]=[CH:11][C:6]([N:1]6[CH2:5][CH2:4][CH2:3][CH2:2]6)=[CH:7][CH:8]=5)=[CH:13][C:14]=3[N:23]=[CH:40]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:31]([CH3:39])([CH3:38])[C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:26]([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 18365552HCID 18365552, compoundHCID 178516822HCID 178516822, compound2×

Product 1

HCID 18365546HCID 18365546, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-pyrrolidinophenyl)-1,2-naphthoquinone-2-oxime (0.005 mol) and 1-isobutyl-3,3-dimethyl-2-methyleneindoline (0.005 mol) in anhydrous ethanol (70 cm3) was refluxed until examination of the reaction mixture by thin layer chromatography indicated that none of the 4-(4-pyrrolidinophenyl)-1,2-naphthoquinone-2-oxime remained. The mixture was cooled, reduced in volume and the precipitated product collected by vacuum filtration washed with a little cold ethanol and dried. Yield=19%, m.p.=242-245° C., λmax=614 nm in PhMe upon irradiation.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitated product collected by vacuum filtration
  3. washwashed with a little cold ethanol
  4. customdried
  5. customYield=19%, m.p.=242-245° C., λmax=614 nm in PhMe upon irradiation

Sources & evidence

ORD record
ord-74add49bef1d4764929ff395bb738cc6
Source dataset
uspto-grants-2001_10
Patent number
US06303673B1

Reaction notes

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