HCID 67264525, compound → HCID 66830037, compound

HRID 1687055Notes

Reaction equation

HRID 1687055 reaction equation
[CH2:1]([N:3]1[CH:9]=[CH:8][C:7]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:6]=2[CH2:5][C:4]1=[O:16])[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:6]=2[CH2:5][C:4]1=[O:16])[CH3:2]

Participants

4

Reactant 1

HCID 67264525HCID 67264525, compound

Product 1

HCID 66830037HCID 66830037, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-ethyl-8-methoxy-1,3-dihydro-benzo[d]azepin-2-one (2.20 g, 0.010 mol) in acetic acid (30 mL) was added palladium 10% wt on carbon (50% wet; 200 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (50 PSI) for 1 day. The reaction mixture was filtered through Celite, concentrated, and subjected to flash chromatography on SiO2 (ethyl acetate/hexanes 20-70%) to give 3-ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (1.33 g, 60%), as a white solid. m.p. ° C.; 1H-NMR (CDCl3) δ 7.00 (d, J=8.3 Hz, 1H), 6.75 (d, J=8.6 Hz, 1H), 3.85 (s, 2H), 3.78 (s, 3H), 3.69 (t, J=6.1 Hz, 2H), 3.48 (q, J=7.3 HZ, 2H), 3.08 (t, J=5.8 Hz, 2H), 1.16 (t, J=7.3 Hz, 3H); LC/MS (ESI+): 220.06 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dd827936753b4dbe871adf722bf49d4f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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