Methanol → 3-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester

HRID 1687785Notes

Reaction equation

HRID 1687785 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].CO>[Pd]>[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 672634723-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester

Product 1

HCID 672645533-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester (338 mg, 1.27 mmol) was placed in methanol (10.0 mL, 0.247 mol) and 10% Palladium on Carbon (50% Wet) (67.5 mg) was added. The reaction was hydrogenated at 25 psi. for 30 minutes and then filtered through a pad of celite to remove the catalyst. The product was then concentrated under reduced pressure to obtain 3-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester as a light brown solid (300 mg, 100%). m.p.=140-143° C.; LCMS (m/e) 237 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 7.18-6.91 (m, 1H), 6.41-6.30 (m, 2H), 4.30-3.93 (m, 4H), 3.83-3.50 (m, 4H), 2.13-1.93 (m, 2H), 1.40-1.10 (m, 3H).

Workup

  1. filtrationfiltered through a pad of celite
  2. customto remove the catalyst
  3. concentrationThe product was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b43cf8e9c7143da9fd840acdb7572be
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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