Triethylamine → 3-(3-Methoxypropoxy)aniline

HRID 1685111Notes

Reaction equation

HRID 1685111 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59292404HCID 59292404, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 433658763-(3-Methoxypropoxy)anilineYield 93.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

1-(3-methoxypropoxy)-3-nitrobenzene (10A) (2.0 g, 11.84 mmol) and tin chloride dihydrate (13.36 g, 59.18 mmol) in 25 mL of ethyl acetate was combined. The mixture was heated at 60° C. for about two hours. The reaction was then chilled at 0° C. Triethylamine (25-30 mL) was added slowly until a white precipitate formed. The white precipitate was filtered over a Celite plug, washed with brine, and then dried over MgSO4. The dried filtrate was then concentrated in vacuo and dried under vacuum to provide 10B (2.0 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.90 (q, J=6.32 Hz, 2H) 3.24 (s, 3 H) 3.44 (t, J=6.32 Hz, 2H) 3.89 (t, J=6.44 Hz, 2H) 5.02 (br. s., 2H) 6.05 (dd, J=8.08, 1.26 Hz, 1H) 6.11-6.14 (m, 2H) 6.87 (t, J=8.21 Hz, 1H). ESI-MS: m/z 182.3 (M+H)+.

Workup

  1. temperatureThe reaction was then chilled at 0° C
  2. customformed
  3. filtrationThe white precipitate was filtered over a Celite plug
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe dried filtrate was then concentrated in vacuo
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5b9b3114fdef42c09f155a55797e3f8e
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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