3-Ethylaniline → (2,2-Diethoxyethyl)-(3-ethylphenyl)amine

HRID 2215823Notes

Reaction equation

HRID 2215823 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])[CH3:2].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([CH2:1][CH3:2])[CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 114753-EthylanilineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium Bicarbonate

Product 1

HCID 21949966(2,2-Diethoxyethyl)-(3-ethylphenyl)amineYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 250-mL round bottom flask was added 3-ethylaniline (10.1 g, 83.2 mmol), bromoacetaldehyde diethyl acetal (10.8 g, 54.8 mmol) and sodium bicarbonate (7.04 g, 83.8 mmol) in absolute ethanol (40 mL). The resulting mixture was stirred at reflux for 5 d. The mixture was concentrated, diluted with ether (30 mL) and washed with water (2×60 mL). The organic solution was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by flash chromatography (SiO2, 5% then 15% EtOAc/hexanes) to give the title compound (4.5 g, 75%) as a white solid. 1H NMR (DMSO-d6) δ 6.98 (m, 1H), 6.42 (m, 2H), 5.34 (m, 1H), 4.53 (m, 1H), 3.59–3.35 (m, 4H), 3.19 (m, 2H), 2.41 (m, 2H), 1.17 (m, 9H).

Workup

  1. temperatureat reflux for 5 d
  2. concentrationThe mixture was concentrated
  3. additiondiluted with ether (30 mL)
  4. washwashed with water (2×60 mL)
  5. dry with materialThe organic solution was dried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was purified by flash chromatography (SiO2, 5%

Sources & evidence

ORD record
ord-519504fdf62345d8b9ff2882a2dd5b76
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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