HCID 68604687, compound → HCID 86604642, compound

HRID 2267645Notes

Reaction equation

HRID 2267645 reaction equation
[CH2:1]([O:3][CH:4]([O:22][CH2:23][CH3:24])[CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)[CH3:2]>C(O)(=O)C.[Pd]>[CH2:23]([O:22][CH:4]([O:3][CH2:1][CH3:2])[CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])[CH3:24].[C:4]([O-:22])(=[O:3])[CH3:5]

Participants

4

Reactant 1

HCID 68604687HCID 68604687, compound

Product 1

HCID 86604642HCID 86604642, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-(3,3-diethoxy-2-phenylpropyl)-2-nitrobenzene (11.74 g, 30.5 mmol) (79a) in acetic acid (30 mL) was hydrogenated under hydrogen atmosphere (40 psi) in the presence of Pd/C (100 mg) for 16 h. At the end of this period the reaction mixture was filtered through a pad of diatomaceous earth and the pad was washed with acetic acid. Upon concentration under reduced pressure the title compound was obtained (11.36 g). 1H NMR (300 MHz, CDCl3) δ 0.86 (t, 3H, J=10 Hz), 1.30 (t, 3H, J=7 Hz), 2.27 (dd, 1H, J=11 Hz, J=14 Hz), 3.08 (dd, 1H, J=3 Hz, J=14 Hz), 3.62 (dt, 1H, J=11, 15 Hz), 3.84 (m, 3H), 4.27 (q, 1H, J=7 Hz), 6.36 (m, 2H), 6.61 (d, 1H, J=8 Hz), 6.87-7.26 (m, 5H). MS APCI, m/z=356 (M+1). LC/MS: 2.11 min.

Workup

  1. customfor 16 h
  2. filtrationAt the end of this period the reaction mixture was filtered through a pad of diatomaceous earth
  3. washthe pad was washed with acetic acid
  4. concentrationUpon concentration under reduced pressure the title compound
  5. customwas obtained (11.36 g)
  6. custom2.11 min.

Sources & evidence

ORD record
ord-fe00a0a440194ef1b4f2de3f608667a0
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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