Sodium Hydroxide → 4-[2-(Pyridin-2-yloxy)ethoxy]aniline

HRID 2111799Notes

Reaction equation

HRID 2111799 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 690616702-[2-(4-Nitrophenoxy)ethoxy]pyridine

Product 1

HCID 690679354-[2-(Pyridin-2-yloxy)ethoxy]aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[2-(4-Nitrophenoxy)ethoxy]pyridine (100 mg, 0.38 mmol) and tin (II) chloride dihydrate (433 mg, 1.92 mmol) were dissolved in ethanol (1.5 mL) and refluxed under nitrogen for 18 h. The reaction mixture was basified to pH 12 with 3M aqueous sodium hydroxide solution. The reaction mixture was stirred for 1 h and then filtered through Celite. The reaction mixture was concentrated in vacuo and the aqueous layer was separated and extracted with CH2Cl2 (5×). The combined organic extracts were concentrated in vacuo to give 4-[2-(pyridin-2-yloxy)ethoxy]aniline as a purple glassy solid. 1H NMR (d6-DMSO, 400 MHz): δ 8.16 (ddd, J=5.2, 2.0, 0.8 Hz, 1H), 7.71 (ddd, J=9.2, 7.2, 2.0 Hz, 1H), 6.99 (ddd, J=7.2, 5.2, 1.0 Hz, 1H), 6.85 (ddd, J=8.4, 0.8, 0.8 Hz, 1H), 6.68 (ddd, J=5.6, 3.6, 3.6 Hz, 2H), 6.50 (ddd, J=5.6, 3.6, 3.6 Hz, 2H), 4.62 (brs, 2H), 4.50 (m, 2H), 4.15 (m, 2H).

Workup

  1. temperaturerefluxed under nitrogen for 18 h
  2. filtrationfiltered through Celite
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe aqueous layer was separated
  5. extractionextracted with CH2Cl2 (5×)
  6. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-597b4c7dcaae423899d59cf615b7cc07
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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