Water → HCID 19359041, compound

HRID 376750Notes

Reaction equation

HRID 376750 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[CH3:13][C:14]1[NH:15][CH:16]=[C:17]([CH3:21])[C:18]=1[CH2:19][CH3:20].O>C(O)(=O)C.ClCCl>[CH2:19]([C:18]1[C:17]([CH3:21])=[C:16]([C:3]2[C:4](=[O:11])[C:5]3[C:10]([C:1](=[O:12])[CH:2]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:15][C:14]=1[CH3:13])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 85301,4-NaphthoquinoneHCID 10600Kryptopyrrole

Product 1

HCID 19359041HCID 19359041, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

6.32 millimol of 1,4-naphthoquinone and 3.16 millimol of 2,4-dimethyl-3-ethylpyrrole were stirred in 20 ml of glacial acetic acid in a round-bottomed flask for 10 minutes at room temperature. The reaction mixture was diluted with 300 ml of dichloromethane and the resulting mixture was then poured into a large volume of water (300 ml). The organic phase was then separated out and washed four times with 100 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2SO4 and then concentrated under vacuum. The product 2-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone was thus isolated in a yield of 80% after purification by chromatography on a column of silica.

Workup

  1. customThe organic phase was then separated out and
  2. washwashed four times with 100 ml of water
  3. dry with materialThe resulting organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0b4dfe39202a4b46a237c142aec587a7
Source dataset
uspto-grants-2000_02
Patent number
US06022379

Reaction notes

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