Hydrochloric Acid → HCID 126796970, compound

HRID 1181394Notes

Reaction equation

HRID 1181394 reaction equation
[N+:1]([CH2:4][CH:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)([O-])=O.[ClH:16]>C(O)C.[Ni]>[ClH:16].[CH:12]1[C:9]2[CH2:10][CH2:11][CH:5]([CH2:4][NH2:1])[CH2:6][CH2:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131726646HCID 131726646, compound

Product 1

HCID 126796970HCID 126796970, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of 7-(nitromethyl)-6,7,8,9-tetrahydro-5H-benzo[α][7]annulene (Description 27; 48.6 g, 0.24 mol) and Ra—Ni (50 g) in ethanol (600 ml) was hydrogenated at 60 psi for 12 hours. An additional charge of Ra—Ni (50 g) was added and the mixture was hydrogenated until GC analysis indicated the reaction was complete. The resulting mixture was filtered over Celite™ and washed with ethanol (200 ml). The filtrate was treated with concentrated HCl (35 ml, 0.42 mol) and concentrated under reduced pressure. The product was then slurried in tert-butyl methyl ether (100 ml) and cooled between 0 and 5° C., filtered and washed with tert-butyl methyl ether (100 ml) and dried to give the title compound (21 g, 42%).

Workup

  1. additionwas added
  2. filtrationThe resulting mixture was filtered over Celite™
  3. washwashed with ethanol (200 ml)
  4. concentrationconcentrated under reduced pressure
  5. temperaturecooled between 0 and 5° C.
  6. filtrationfiltered
  7. washwashed with tert-butyl methyl ether (100 ml)
  8. customdried

Sources & evidence

ORD record
ord-f02f093bf0a843d2af5a949cca5b4c35
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

Loading…