4-Aminophenol → 4-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

HRID 1042790Notes

Reaction equation

HRID 1042790 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:16]1[CH:17]=[CH:18][N:19]=[C:20]2[C:25]=1[N:24]=[CH:23][C:22]([O:26][CH3:27])=[CH:21]2>CN(C=O)C>[CH3:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[CH:17][CH:18]=[N:19]2)=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 441851064-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alternatively, the title compound may be prepared by the following method: In a nitrogen purged sealed pressure vessel, dissolved 4-aminophenol (0.617 g, 5.65 mmol) in DMF (0.030 L). Cesium carbonate (3.68 g, 11.3 mmol) was added and the mixture was stirred at RT for 5 min. Added 8-chloro-3-methoxy-1,5-naphthyridine (1.00 g, 5.14 mmol), heated to 90° C., stirred for 17 h. The mixture was allowed to cool to RT and was concentrated. The crude material was triturated with methanol, filtered, washed with methanol followed by water, and air dried to yield 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as brown solid. MS [M+H]=268.1; Calc'd 267.3 for C15H13N3O2.

Workup

  1. customIn a nitrogen purged
  2. customsealed pressure vessel
  3. stirringstirred for 17 h
  4. temperatureto cool to RT
  5. concentrationwas concentrated
  6. customThe crude material was triturated with methanol
  7. filtrationfiltered
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-b2266c36990244c188caad0d936b3dff
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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