4-Amino-3-Nitrophenol → 2-Nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine

HRID 1790684

Reaction equation

HRID 1790684 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:15][N:14]=1>CN(C)C=O>[N+:9]([C:3]1[CH:4]=[C:5]([O:8][C:13]2[N:18]=[C:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[CH:7][C:2]=1[NH2:1])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 37588824-Amino-3-NitrophenolHCID 118055432-Chloro-4-(pyridin-3-yl)pyrimidine

Product 1

HCID 220413402-Nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-3-nitro-phenol (1 eq) and 2-chloro-4-(3-pyridyl)pyrimidine (1 eq) in N,N-dimethylformamide was microwaved at 150° C. for 10 mins. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was concentrated and purified on silica gel to yield 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine. MS: MH+=309.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationThe organic layer was concentrated
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-489fdd3767e74cdab1836ba0effdcde5
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Linked notes

Loading…