Methane → HCID 131715725, compound

HRID 867516Notes

Reaction equation

HRID 867516 reaction equation
[CH:1]1([C:6]2([CH3:22])[CH2:14][C:13]3[C:8](=[C:9]([Cl:20])[C:10]([Cl:19])=[C:11]([O:15][CH2:16][C:17]#[N:18])[CH:12]=3)[C:7]2=[O:21])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].[Cl-:24].[NH4+:25].C>CO.O1CCOCC1>[OH2:15].[ClH:19].[CH:1]1([C:6]2([CH3:22])[CH2:14][C:13]3[C:8](=[C:9]([Cl:20])[C:10]([Cl:19])=[C:11]([O:15][CH2:16][C:17](=[NH:25])[NH2:18])[CH:12]=3)[C:7]2=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5]1.[CH:1]1([C:6]2([CH3:22])[CH2:14][C:13]3[C:8](=[C:9]([Cl:20])[C:10]([Cl:19])=[C:11]([O:15][CH2:16][C:17](=[NH:25])[NH2:18])[CH:12]=3)[C:7]2=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5]1.[ClH:24]

Participants

7

Reactant 4

HCID 297MethaneHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 12395633HCID 12395633, compound

Product 1

HCID 131715725HCID 131715725, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of [(2-cyclopentyl-6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]acetonitrile (3.88 g, 10 mmole; see Example 1) in methanol (50 ml) was added sodium metal (0.1 g, 4 mg-atom), and the mixture was stirred for one hour. Ammonium chloride (0.6 g, 11 mmole) was added and the mixture was stirred overnight. The mixture was concentrated to dryness in vacuo, and the resultant residue was triturated with boiling benzene, then collected by filtration. The solid was dissolved in a minimum amount of dimethylformamide and filtered. The filtrate was diluted with diethyl ether (100 ml), giving an oil from which the ether supernatant was removed by decanting. Trituration with warm benzene gave a solid. The ether than was removed by decanting produced an additional quantity of the oil, which solidified on standing. The solids were combined and dissolved in boiling dioxane (50 ml). The cloudy solution was decolorized with charcoal, filtered, and diluted with benzene to yield a white solid. Drying at 80° at 1 mm Hg pressure produced the title compound (ca. 1.7 g) as an analytically pure solid.

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe mixture was concentrated to dryness in vacuo
  3. customthe resultant residue was triturated with boiling benzene
  4. filtrationcollected by filtration
  5. dissolutionThe solid was dissolved in a minimum amount of dimethylformamide
  6. filtrationfiltered
  7. additionThe filtrate was diluted with diethyl ether (100 ml)
  8. customgiving an oil from which the ether supernatant
  9. customwas removed
  10. customby decanting
  11. customTrituration with warm benzene gave a solid
  12. customThe ether than was removed
  13. customby decanting
  14. customproduced an additional quantity of the oil, which
  15. dissolutiondissolved
  16. filtrationfiltered
  17. additiondiluted with benzene
  18. customto yield a white solid
  19. customDrying at 80° at 1 mm Hg pressure

Sources & evidence

ORD record
ord-84f0c502a4264e75b493296e74ff63a1
Source dataset
uspto-grants-1988_10
Patent number
US04775695

Reaction notes

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