3-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene → 6,7,8,9-Tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

HRID 1041696Notes

Reaction equation

HRID 1041696 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-])=O>[Pd].C(O)C>[CH:13]1[C:7]2[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([NH2:1])[CH:14]=1

Participants

4

Reactant 1

HCID 672641803-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Product 1

HCID 672637576,7,8,9-Tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (281 mg, 1.45 mmol) and 10% Palladium on Carbon (50% Wet) (77 mg) in Ethanol (10 mL) was shaken under an atmosphere of Hydrogen (50 psi) for 5 h, filtered and conc. to give 6,7,8,9-Tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine (230 mg, 97%). 1H-NMR (CDCl3): 6.58 (d, 1H, J=8.1 Hz), 6.40 (s, 1H), 6.27 (d, 1H, J=8.1 Hz), 4.01 (m, 2H), 3.39 (br s, 3H), 3.10 (m, 2H), 1.97 (m, 2H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-665f6faed6db4dbd95e491b5eb4ff3a8
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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