Quinone → HCID 131713950, compound

HRID 1633155Notes

Reaction equation

HRID 1633155 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](OCC)=O)=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=1.[C:25]1(=[O:32])[CH:30]=[CH:29][C:28](=O)[CH:27]=[CH:26]1.C(=O)(O)[O-:34].[Na+].[CH3:38][C:39](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:40]>O>[CH2:39]([O:40][C:25]([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:19]1[C:18]([OH:34])=[CH:17][CH:16]=[C:15]2[C:20]=1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[NH:14]2)=[O:32])[CH3:38]

Participants

6

Reactant 4

HCID 4650QuinoneHCID 516892Sodium BicarbonateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 70505436HCID 70505436, compound

Product 1

HCID 131713950HCID 131713950, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.334 g of ethyl β-(3-pyridyl)-β-(5-ethoxycarbonylpentylamino)acrylate and 0.108 g of p-benzoquinone in 1 ml of glacial acetic (according to the general procedure as described in J. Chem. Soc. C 1968, 1795) is heated at 60° for 4 hours. The reaction mixture is cooled, diluted with 10 ml of water, neutralized to pH 7 with saturated sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extract is dried, evaporated to dryness and the resulting product is purified by preparative TLC (silica gel; ethyl acetate, hexane 1:1) to give 1-(5-ethoxycarbonylpentyl-3-ethoxycarbonyl-5-hydroxy-2-(3-pyridyl)indole, NMR δ3.95, 4.1, 8.75.

Workup

  1. temperatureC 1968, 1795) is heated at 60° for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. customis dried
  6. customevaporated to dryness
  7. customthe resulting product is purified by preparative TLC (silica gel; ethyl acetate, hexane 1:1)

Sources & evidence

ORD record
ord-501ca7e0789f4a77866f62747bbd9fa8
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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