4-Chloropyridine hydrochloride → 1-Amino-4-(4-pyridinyl)oxynaphthalene

HRID 1884599Notes

Reaction equation

HRID 1884599 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][CH:4]=1.Cl.Cl[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>CN1C(=O)CCC1.O.ClCCl>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 818524-Chloropyridine hydrochlorideHCID 27238584-Amino-1-naphthol hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 235058621-Amino-4-(4-pyridinyl)oxynaphthaleneYield 16.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 4-amino-1-naphthol hydrochloride (2.5 g, 12.8 mmol) and 4-chloropyridine hydrochloride (3.84 g, 29.2 mmol) in NMP (20 mL) was added potassium tert-butoxide (6.0 g, 53.47 mmol) slowly. The mixture was heated at 120° C. for 6 h, cooled to room temperature and diluted with water and dichloromethane. The combined organic extracts were washed with HCl (2N), saturated aqueous NaHCO3 and brine and dried (Na2SO4). Removal of the volatiles in vacuo afforded the product (0.5 g, 16%).

Workup

  1. temperaturecooled to room temperature
  2. washThe combined organic extracts were washed with HCl (2N), saturated aqueous NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-41e3f3a2a8574a7d9c25ebafb92e4632
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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