HCID 54074187, compound → HCID 86756084, compound

HRID 1274527Notes

Reaction equation

HRID 1274527 reaction equation
C(N(CC)[C:4]1[CH:28]=[CH:27][C:7]2[C:8](=[O:26])[C:9](=[C:11]3[C:15](=[O:16])[C:14]4[CH:17]=[CH:18][C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:20][C:13]=4[O:12]3)[O:10][C:6]=2[CH:5]=1)C>C(O)(=O)C.[Zn]>[CH2:24]([N:21]([CH2:22][CH3:23])[C:19]1[CH:18]=[CH:17][C:14]2[C:15](=[O:16])[C:11](=[C:9]3[C:8](=[O:26])[C:7]4[CH:27]=[CH:28][CH:4]=[CH:5][C:6]=4[O:10]3)[O:12][C:13]=2[CH:20]=1)[CH3:25]

Participants

4

Reactant 1

HCID 54074187HCID 54074187, compound

Product 1

HCID 86756084HCID 86756084, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

0.10 g of the oxindigo 1a (from Example 14) is dissolved in 40 ml of glacial acetic acid. 1.67 g (25.5 mmol) of zinc powder are introduced into the dark red solution. After the solution has been heated to the boiling point, it gradually becomes yellow in colour. The zinc sediment is filtered off to give a clear, dark yellow solution of blue fluorescence. A cotton ribbon is impregnated in this solution for 15 minutes. Chiefly the blue cis form 2a is then formed by oxidation in the air. During a couple of months in air and sunlight (during days) visually no color change is observed.

Workup

  1. temperatureAfter the solution has been heated to the boiling point, it gradually becomes yellow in colour
  2. filtrationThe zinc sediment is filtered off
  3. customto give a clear, dark yellow solution of blue fluorescence

Sources & evidence

ORD record
ord-91beb81fe2674082954fa55c20d71c1f
Source dataset
uspto-grants-2000_12
Patent number
US06156914

Reaction notes

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