HCID 67263730, compound → 9-Methyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-2-ylamine

HRID 1688023Notes

Reaction equation

HRID 1688023 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1>[Pd].C(O)C>[CH3:1][N:2]1[C:8]2[CH:9]=[C:10]([NH2:13])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 67263730HCID 67263730, compound

Product 1

HCID 672646829-Methyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-2-ylamineYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9-Methyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.296 g, 1.42 mmol) and 10% Palladium on Carbon (50% Wet) (0.097 g) in Ethanol (20 mL) was shaken under an atmosphere of Hydrogen (30 psi) overnight. The mixture was filtered, washing with 20 mL ethanol. The filtrate was concentrated to give 9-Methyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-2-ylamine as a white solid (206 mg, 81%). 1H-NMR (CDCl3): 6.77 (d, 1H, J=8.2 Hz), 6.21 (s, 1H), 6.14 (d, 1H, J=8.2 Hz), 3.96 (t, 2H, J=5.5 Hz), 3.35 (br s, 2H), 3.09 (t, 2H, J=5.6 Hz), 2.86 (s, 3H), 1.99 (tt, 2H, J=5.5, 5.6 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with 20 mL ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-021711d6f36f4a3d9405d26a063f81d0
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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