HCID 21188012, compound → HCID 21188010, compound

HRID 1383436Notes

Reaction equation

HRID 1383436 reaction equation
C([C:4]1[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1C(O)=O)(O)=O>N1C2C(=CC=CC=2)C=CC=1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:5]1[CH:4]=[CH:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6]1

Participants

3

Reactant 1

HCID 21188012HCID 21188012, compound

Product 1

HCID 21188010HCID 21188010, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

4.8 g of 2,3-dicarboxy-1-(2-methoxyphenyl)-4-phenyl-pyrrole and 2 g of Cu powder are heated for 2 hours to about 200° C. in 50 ml of quinoline. After cooling the Cu powder is filtered off. The filtrate is diluted with water, acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase is washed successively with dilute, aqueous HCl solution, NaHCO3 solution and water and then dried. After the solvent has been distilled off in vacuo the remaining product is purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5). 1.6 g of 1-(2-methoxyphenyl)-3-phenyl-pyrrole are obtained in the form of a colourless oil.

Workup

  1. filtrationis filtered off
  2. additionThe filtrate is diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed successively
  5. additionwith dilute
  6. dry with materialaqueous HCl solution, NaHCO3 solution and water and then dried
  7. distillationAfter the solvent has been distilled off in vacuo the remaining product
  8. customis purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-d3998b65f8e549119c667146f17f3903
Source dataset
uspto-grants-2001_07
Patent number
US06255327B1

Reaction notes

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