4-Aminophenol → 4-(2-Chloro-pyridin-4-yloxy)-phenylamine

HRID 1098543Notes

Reaction equation

HRID 1098543 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=1>CN(C=O)C>[Cl:15][C:16]1[CH:21]=[C:20]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 335152,4-DichloropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 578334304-(2-Chloro-pyridin-4-yloxy)-phenylamineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-amino-phenol (8.9 g, 81.6 mmol) and potassium tert-butoxide (10.7 g, 95.2 mmol) were suspended in DMF (100 mL) and stirred at RT for 30 min. 2,4-Dichloro-pyridine (10 g, 68 mmol) was added and the resulting mixture was heated to 90° C. for 3 h. The solvent was removed under vacuum and the residue was extracted with DCM (2×100 mL). The combined organics were dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to afford 4-(2-chloro-pyridin-4-yloxy)-phenylamine (9.0 g, 60% yield). 1H NMR (DMSO-d6): δ 8.21 (d, J=5.6 Hz, 1 H), 6.85-6.82 (m, 4 H), 6.61 (d, J=6.6 Hz, 2 H), 5.17 (s, 2 H); MS (ESI) m/z: 221 (M+H+).

Workup

  1. temperaturethe resulting mixture was heated to 90° C. for 3 h
  2. customThe solvent was removed under vacuum
  3. extractionthe residue was extracted with DCM (2×100 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f71fe5b6a4f747ea80538201d5431a19
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

Loading…