HCID 67263706, compound → HCID 67263926, compound

HRID 1040611Notes

Reaction equation

HRID 1040611 reaction equation
[H][H].[CH2:3]([N:5]1[CH2:15][CH:14]2[O:16][CH:7]([C:8]3[C:13]2=[CH:12][C:11]([N+:17]([O-])=O)=[CH:10][CH:9]=3)[CH2:6]1)[CH3:4]>[Pd].C(O)C.C(Cl)Cl>[CH2:3]([N:5]1[CH2:15][CH:14]2[O:16][CH:7]([C:8]3[C:13]2=[CH:12][C:11]([NH2:17])=[CH:10][CH:9]=3)[CH2:6]1)[CH3:4]

Participants

6

Reactant 2

HCID 67263706HCID 67263706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67263926HCID 67263926, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrogen was bubbled through a mixture of 10-ethyl-4-nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (115 mg, 0.56 mmol) and 10% palladium on carbon (53 mg, 0.050 mmol) in ethanol (3 mL) and CH2Cl2 (3 mL) for 5 min. The reaction was then stirred under a hydrogen atmosphere for 18 h. Filtration through Celite and concentration gave 10-Ethyl-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-trien-4-ylamine as an off-white foam (100 mg, 100%). MS (m/e) 205 (M+1.

Workup

  1. filtrationFiltration
  2. concentrationthrough Celite and concentration

Sources & evidence

ORD record
ord-ed1b650787af4b6a93956455d4018286
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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