Sodium Chloride → HCID 19036548, compound

HRID 264437Notes

Reaction equation

HRID 264437 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]2[C:6]([CH2:7][C:8]3[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C:9]=32)=[CH:5][CH:4]=1.[OH-:21].[K+].[Cl-].[Na+].[CH2:25]([OH:28])[CH2:26]O.[OH2:29]>>[C:16]([OH:18])(=[O:29])/[CH:17]=[CH:26]/[C:25]([OH:28])=[O:21].[CH3:1][O:2][C:3]1[CH:20]=[C:19]2[C:6]([CH2:7][C:8]3[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][NH2:15])[C:9]=32)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036413N-[2-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamideHCID 20437942Ethylene glycol water

Product 1

HCID 19036548HCID 19036548, compoundYield 66%

Procedure

2.4 g of N-[2-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamide were heated to 140° for 17 hours under argon in 48 ml of ethylene glycol/water 2:1 in the presence of 2.5 g of potassium hydroxide. The mixture was left to cool and treated with 250 ml of semi-saturated sodium chloride solution. The mixture was extracted three times with diethyl ether and the combined extracts were dried over sodium sulfate, filtered and evaporated. The brown oil was dissolved in 30 ml of methanol and treated with 1.0 g of fumaric acid, following which pale brown crystals separated. These were dissolved in 120 ml of warm methanol. After cooling to room temperature the product was crystallized out by the slow addition of 120 ml of diethyl ether. 2.0 g (66%) of 2-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethylamine fumarate (1:1) with m.p. 177°-180° were obtained.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. extractionThe mixture was extracted three times with diethyl ether
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe brown oil was dissolved in 30 ml of methanol
  8. additiontreated with 1.0 g of fumaric acid
  9. customseparated
  10. dissolutionThese were dissolved in 120 ml of warm methanol
  11. customwas crystallized out by the slow addition of 120 ml of diethyl ether

Sources & evidence

ORD record
ord-376bb9ccc6ba44b9b8a88e05d6fd4b14
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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