2,4-Dichloropyridine → 4-(2-Chloropyridin-4-yloxy)-3-fluorobenzenamine

HRID 450412Notes

Reaction equation

HRID 450412 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl:10][C:11]1[CH:16]=[C:15](Cl)[CH:14]=[CH:13][N:12]=1>>[Cl:10][C:11]1[CH:16]=[C:15]([O:9][C:3]2[CH:4]=[CH:5][C:6]([NH2:8])=[CH:7][C:2]=2[F:1])[CH:14]=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 335152,4-DichloropyridineHCID 2735918Phenol, 4-amino-2-fluoro-

Product 1

HCID 598529984-(2-Chloropyridin-4-yloxy)-3-fluorobenzenamineYield 67%

Procedure

Using a procedure analogous to Example A1, 2-fluoro-4-aminophenol (2.6 g, 24 mmol) and 2,4-dichloropyridine (2.88 g, 20 mol) were combined to provide 4-(2-chloropyridin-4-yloxy)-3-fluoroaniline (3.2 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.25 (d, J=5.6 Hz, 1H), 6.99 (m, 1H), 6.90 (m, 2H), 6.50 (d, J=1.6 Hz, 1H), 6.41 (d, J=10.4 Hz, 1H), 5.51 (s, 2H); MS (ESI) m/z: 239.1 (M+H+).

Sources & evidence

ORD record
ord-04248402b2e9489c8704889a786bec8b
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

Loading…