HCID 59353071, compound → HCID 59353052, compound

HRID 1914682Notes

Reaction equation

HRID 1914682 reaction equation
[C:1]1(=[CH:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[N+:15]([O-])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[NH2:15])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 59353071HCID 59353071, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59353052HCID 59353052, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(cyclopentylidenemethyl)-4-methoxy-2-nitrobenzene (1.8 g; 0.09 M, 7.72 mmol; 1 eq) in MeOH (80 mL) is pumped through the H-Cube™ flow hydrogenator fitted with a 10 mol % Pd/C catalyst cartridge (30×4 mm) heated to 25° C. at 1 bar with the full hydrogen option enabled. The flow rate is set at 1 mL/min. The catalyst is pre-saturated with hydrogen gas for 2 min before passing the substrate through. The solvent is evaporated under reduced pressure and the residue is taken up in HCl 1N and EtOAc. The organic phase is washed with brine then dried over MgSO4, and the solvent is evaporated under reduced pressure to afford 1.02 g (64%) of the title compound as a brown oil. 1H NMR (CDCl3) δ 6.94 (d, J=8.3 Hz, 1H), 6.45-6.35 (m, 2H), 4.45-3.90 (m, 2H), 3.75 (s, 3H), 2.45 (d, J=7.0 Hz, 2H), 2.12 (q, J=7.0 Hz, 1H), 1.78-1.45 (m, 6H), 1.35-1.05 (m, 2H). HPLC (max plot) 89%; Rt 2.86 min. LC/MS: (ES+): 206.1.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. washThe organic phase is washed with brine
  3. dry with materialthen dried over MgSO4
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-efa63f95961346519f181755f27e20b3
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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