Water → 4-(Benzyloxy)pyridin-3-amine

HRID 595690Notes

Reaction equation

HRID 595690 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-].C1COCC1.O>CO.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 127165204-(Benzyloxy)-3-nitropyridine

Product 1

HCID 288900524-(Benzyloxy)pyridin-3-amineYield 81.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(benzyloxy)-3-nitropyridine (42.0 g, 0.18 mol), Fe (30.6 g, 0.55 mol) and NH4Cl (48.8 g, 0.91 mol) in MeOH:THF:H2O=(2:2:1, 750 mL) was stirred at reflux for 3 h. After being filtered and concentrated in vacuum, the residue was purified by column chromatography (DCM:MeOH=10:1) to give to give the pure 4-(benzyloxy)pyridin-3-amine (29.5 g, yield: 80.7%). 1H-NMR (CDCl3, 400 MHz) δ 8.25 (s, 1H), 7.88 (s, 1H), 7.20˜7.65 (m, 5H), 6.89 (s, 1H), 5.18 (s, 2H). MS (M+H)+: 201.

Workup

  1. temperatureat reflux for 3 h
  2. filtrationAfter being filtered
  3. concentrationconcentrated in vacuum
  4. customthe residue was purified by column chromatography (DCM:MeOH=10:1)
  5. customto give

Sources & evidence

ORD record
ord-94c13b9f600b44dca61f47db0cee8982
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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