HCID 23298410, compound → HCID 23298445, compound

HRID 1953557Notes

Reaction equation

HRID 1953557 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:15]=[CH:14][C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13][C:7]=2[CH:6]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[ClH:1].[CH2:9]1[C:8]2[CH:14]=[CH:15][C:5]([NH2:2])=[CH:6][C:7]=2[CH2:13][CH2:12][NH:11][CH2:10]1

Participants

5

Reactant 2

HCID 23298410HCID 23298410, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23298445HCID 23298445, compoundYield 166.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 2,3,4,5-tetrahydro-7-nitro-1H-3-benzazepine hydrochloride (1.68 g, 7.35 mmol) in ethanol (100 ml) was added 5% palladium on carbon (0.2 g) and the solution was placed on a Paar Hydrogenator Apparatus and pressurized with 45 psi of hydrogen. After the theoretical uptake of hydrogen had been achieved (2 h), the catalyst was filtered off and washed with water (25 ml). The filtrate was concentrated. Absolute ethanol was added and evaporated until all of the water had been evaporated and a solid formed. The solid was dissolved in hot ethanol (50 ml) and the product was precipitated by the addition of ether (75 ml). The solid was collected and air-dried to give the product as an off-white solid (2.43 g (94%)), m.p. 288-91° C.

Workup

  1. custom(2 h)
  2. filtrationthe catalyst was filtered off
  3. washwashed with water (25 ml)
  4. concentrationThe filtrate was concentrated
  5. additionAbsolute ethanol was added
  6. customevaporated until all of the water
  7. customhad been evaporated
  8. customa solid formed
  9. customthe product was precipitated by the addition of ether (75 ml)
  10. customThe solid was collected
  11. customair-dried

Sources & evidence

ORD record
ord-1e48858a9b0d413aa140a4acb7f9fa84
Source dataset
uspto-grants-2000_09
Patent number
US06117898

Reaction notes

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