Ammonium Hydroxide → HCID 56609585, compound

HRID 1110871Notes

Reaction equation

HRID 1110871 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:16].[H-].[Na+].Br[C:20]1[CH:21]=[C:22]([O:26][CH3:27])[CH:23]=[CH:24][CH:25]=1.[NH4+].[OH-]>C(OCC)(=O)C.CN(C)C=O>[CH3:27][O:26][C:22]1[CH:21]=[C:20]([N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[C:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])[C:8]2=[O:16])[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 169713-BromoanisoleHCID 24758Sodium hydrideHCID 56632142HCID 56632142, compound

Product 1

HCID 56609585HCID 56609585, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under N2, 3-(1-methyl-2-pyrrolidinylidene)-2(1H,3H)-indolone (1.0 g, 5 mmoles) was added portionwise to a slurry of NaH (50% oil dispersion>265 mg., 5.5 mmoles) slurried in 50 ml. dimethylformamide and the mixture stirred at 25° for 2 hours. Cu2Br2 (1 43 g, 5 mmoles) and then m-bromoanisole (1.9 ml, 15 mmole) were added. The mixture was heated at 130° for 3.5 days, cooled, poured over ice and ethyl acetate, basified with NH4OH and filtered over a pad of diatomaceous earth. The aqueous layer was separated from the filtrate and extracted with fresh ethyl acetate. The combined organic layers were back-washed with H2O, dried over MgSO4, treated with activated carbon, evaporated to dryness and the residue triturated with ether, and filtered to yield starting material (110 mg). The ether filtrate was evaporated to an oil and chromatographed on 75 ml. silica gel, eluting with CHCl 3. Clean product fractions were combined, evaporated to an oil and crystallized from CHCl3 /ether, 320 mg, m.p. 127°-129° (dec).

Workup

  1. temperatureThe mixture was heated at 130° for 3.5 days
  2. temperaturecooled
  3. filtrationfiltered over a pad of diatomaceous earth
  4. customThe aqueous layer was separated from the filtrate
  5. extractionextracted with fresh ethyl acetate
  6. washThe combined organic layers were back-washed with H2O
  7. dry with materialdried over MgSO4
  8. additiontreated with activated carbon
  9. customevaporated to dryness
  10. customthe residue triturated with ether
  11. filtrationfiltered
  12. customto yield
  13. customThe ether filtrate was evaporated to an oil
  14. customchromatographed on 75 ml
  15. washsilica gel, eluting with CHCl 3
  16. customevaporated to an oil
  17. customcrystallized from CHCl3 /ether, 320 mg, m.p. 127°-129° (dec)

Sources & evidence

ORD record
ord-a13dbb2119254007889ac47b0ece57ad
Source dataset
uspto-grants-1990_12
Patent number
US04977178

Reaction notes

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