Methanol → 2,3,4,5-Tetrahydro-benzo[b]oxepin-9-ylamine

HRID 1041145Notes

Reaction equation

HRID 1041145 reaction equation
[N+:1]([C:4]1[C:9]2[O:10][CH2:11][CH:12]=[CH:13][CH2:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.CO.[H][H]>[Pd]>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([NH2:1])[C:9]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 232472469-Nitro-2,5-dihydrobenzo[b]oxepineHCID 178418361HCID 178418361, compound

Product 1

HCID 137576312,3,4,5-Tetrahydro-benzo[b]oxepin-9-ylamineYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Parr pressure reactor was placed 9-nitro-2,5-dihydro-benzo[b]oxepine (200 mg, 0.001 mol) in methanol (10 mL, 0.3 mol). To this solution was added palladium on carbon 10% (10 mg). The reaction was placed under 50 psi hydrogen and shaken overnight. Reaction mixture was filtered through celite, rinsed with methanol (3×10 mL) and concentrated in vacuo to give 2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine as an off-white solid (142 mg, 83%).

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite
  3. washrinsed with methanol (3×10 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a12aec1cdb4d43cc955ffdcc2f01fb6a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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