HCID 67263870, compound → HCID 67263756, compound

HRID 1040607Notes

Reaction equation

HRID 1040607 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9][C:8]=2[CH:14]=1)([O-])=O.[H][H]>CO.[Pd]>[CH:14]1[C:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 67263870HCID 67263870, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67263756HCID 67263756, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-5,6,8,9-tetrahydro-7-oxa-benzocycloheptene (270 mg/1.3 mmol) was dissolved in anhydrous methanol (ca. 10 mL) and the solution added to a Parr flask. Palladium (10% on charcoal) was added carefully and the mixture shaken under 40 psi of hydrogen for 2 hours. The mixture was then filtered and the colorless filtrate concentrated onto celite. Chromatography on an amine-bonded column (eluting with 0→60% ethyl acetate/hexanes) afforded 5,6,8,9-tetrahydro-7-oxa-benzocyclohepten-2-ylamine as a colorless solid (200 mg/quantitative). 1H NMR (400 MHz, CDCl3) δ 6.89 (d, J=7.6 Hz, 1H), 6.42 (m, 2H), 3.78 (m, 4H), 3.55 (br s, 2H), 2.88 (m, 4H).

Workup

  1. additionthe solution added to a Parr flask
  2. filtrationThe mixture was then filtered
  3. concentrationthe colorless filtrate concentrated onto celite
  4. washChromatography on an amine-bonded column (eluting with 0→60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9c7cdc3d7708492c968b7320e68e2fb3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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