1-Cyclopentyloxy-2-methoxy-5-nitrobenzene → 3-(Cyclopentyloxy)-4-methoxyaniline

HRID 750986Notes

Reaction equation

HRID 750986 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=2[O:16][CH3:17])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([O:6][C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][C:8]=2[O:16][CH3:17])[NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 113907411-Cyclopentyloxy-2-methoxy-5-nitrobenzene

Product 1

HCID 27793343-(Cyclopentyloxy)-4-methoxyanilineYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 10% Pd on activated carbon (25 g) in ethanol (4 L), under N2 protection, was added 1-cyclopentyloxy-2-methoxy-5-nitrobenzene (250 g, 1.054 mol). The reaction mixture was degassed under vacuum three times. The reaction mixture was stirred vigorously while hydrogen gas was allowed to flow over the reaction mixture. After 4 h the reaction was complete by TLC (5:1 hex:EA). The reaction mixture was filtered through a pad of celite and the celite was rinsed with additional ethanol. The solvent was removed in-vacuo to obtain 208.38 g (95% yield) of 3-cyclopentyloxy-4-methoxyaniline as a red liquid. 1H NMR (CDCl3) δ 6.85 (d. J=8.4 Hz, 1H), 6.29 (s, 1H), 6.19 (dd, J=2.8, 8.4, 1H), 4.69 (p, J=4.4 Hz, 1H), 3.75 (s, 3H), 3.44 (bs, 2H), 1.90-1.81 (m, 6H), 1.61-1.55 (m, 2H).

Workup

  1. customThe reaction mixture was degassed under vacuum three times
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe celite was rinsed with additional ethanol
  4. customThe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-2e0927ad6b334182a69b62c7395b9e43
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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