9-Ethyl-3-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene → 9-Ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

HRID 1688002Notes

Reaction equation

HRID 1688002 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-])=O)=[CH:13][C:8]=2[O:7][CH2:6][CH2:5][CH2:4]1)[CH3:2]>[Pd].C(O)C>[CH2:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:8]=2[O:7][CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 672639069-Ethyl-3-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Product 1

HCID 672640069-Ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9-Ethyl-3-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.865 g, 3.89 mmol) and 10% Palladium on Carbon (50% Wet) (0.400 g) in Ethanol (25 mL) were shaken under an atmosphere of Hydrogen (40 psi). After 2 h, the mixture was filtered through Celite, washing with ethanol. Conc. in vacuo afforded 9-Ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine in quantitative yield. 1H-NMR (CDCl3): 6.75 (d, 1H, J=8.0 Hz), 6.32 (m, 2H), 4.04 (t, 2H, J=5.4 Hz), 3.43 (s, 2H), 3.09 (m, 4H), 1.96 (m, 2H), 1.14 (t, 3H, J=7.1 Hz).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. washwashing with ethanol

Sources & evidence

ORD record
ord-db4320348947414ba886d8b06eb7c1d3
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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