HCID 67264019, compound → 9-Ethyl-2-fluoro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

HRID 1687989Notes

Reaction equation

HRID 1687989 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([F:17])[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]=[C:11]([F:17])[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 67264019HCID 67264019, compound

Product 1

HCID 672638939-Ethyl-2-fluoro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9-Ethyl-2-fluoro-3-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (515 mg, 2.14 mmol) and 10% Palladium on Carbon (50% Wet) (0.25 g) in Ethanol (30 mL) were shaken under an atmosphere of Hydrogen (40 psi) for 4 h. The mixture was filtered through Celite, washing with ethanol, and conc. in vacuo to afford 9-Ethyl-2-fluoro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine as a green film (0.375 g, 84%). 1H-NMR (CDCl3): 6.60 (d, 1H, J=12.8 Hz), 6.44 (d, 1H, J=9.2 Hz), 3.99 (m, 2H), 3.42 (s, 1H), 3.09 (m, 4H), 1.96 (m, 2H), 1.56 (m, 2H), 1.17 (t, 3H, J=7.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-7b030886de784943aad528580df92055
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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