HCID 67263463, compound → HCID 67264481, compound

HRID 1041692Notes

Reaction equation

HRID 1041692 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]([CH2:18][OH:19])([OH:17])[CH2:4]1)[CH3:2]>C(O)C.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]2[O:7][CH2:6][C:5]([CH2:18][OH:19])([OH:17])[CH2:4][N:3]([CH2:1][CH3:2])[C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 67263463HCID 67263463, compound

Product 1

HCID 67264481HCID 67264481, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenation of 9-Ethyl-7-hydroxymethyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ol (0.225 g, 0.839 mmol) in Ethanol (15 mL) with 10% Palladium on Carbon (50% Wet) (89 mg) under an atmosphere of Hydrogen (40 psi) for 6 h followed by filtration gave 2-Amino-9-ethyl-7-hydroxymethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ol in quantitative yield as an oil (199 mg). 1H-NMR (DMSO): 9.7 (br s, 3H), 6.80 (d, 1H, J=8.2 Hz), 6.64 (s, 1H), 6.51 (d, 1H, J=8.2 Hz), 3.96 (d, 1H, J=12 Hz), 3.81 (d, 1H, J=12 Hz), 3.22 (m, 6H), 1.05 (m, 3H).

Sources & evidence

ORD record
ord-48d5956978f74dda87e03a1feb9b773e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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