3-Nitrophenylethyl alcohol → 2-(3-Aminophenyl)ethan-1-ol

HRID 480649Notes

Reaction equation

HRID 480649 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9]

Participants

4

Reactant 1

HCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 149389872-(3-Aminophenyl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Nitrophenethyl alcohol (1.50 g) is added to a suspension of Pd/C (10%, 500 mg) in ethanol (15 mL). The mixture is placed under hydrogen gas pressure (35 psi) in a Parr hydrogenator for 1 h. The catalyst is removed by filtration through Celite and the solution is concentrated to afford 3-aminophenethyl alcohol. Condensation with the resulting crude aniline according to the general procedure at room temperature for 36 followed by purification by column chromatography (CH2Cl2/methanol, 100/1; 50/1; 33/1; 20/1) affords 2.94 g (78%) of the title compound as an orange amorphous solid. Physical characteristics: 1H NMR (400 MHz, DMSO-d6) δ 12.26, 10.82, 8.53, 8.41, 7.46-7.26, 7.19-7.06, 4.68, 3.99-3.92, 3.67-3.61, 3.58, 3.48, 2.77, 2.36, 0.93, 0.82; IR (liq.) 1696, 1672, 1627 (s), 1610 (s), 1591 (s), 1571 (s), 1494, 1428 (s), 1301 (s), 1281 (s), 1259 (s), 1233, 1208, 1117 (s), 1104 cm-; MS (ESI+) m/z 457 (100, (M+H)+), 458 (25). HRMS calcd for C25H29FN2O5+H m/z 457.2138, found 457.2143.

Workup

  1. customfor 1 h
  2. customThe catalyst is removed by filtration through Celite
  3. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-8af40739522b41d5a44143809c6fbf9a
Source dataset
uspto-grants-2003_11
Patent number
US06653307B2

Reaction notes

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