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

HRID 1041681Notes

Reaction equation

HRID 1041681 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-9d44139ed6e44381b2ca7451c35d5937
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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