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

HRID 1042789Notes

Reaction equation

HRID 1042789 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.O>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

6

Reactant 4

HCID 4034-AminophenolHCID 962WaterHCID 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

Five 20 mL microwave vials were each charged with 4-aminophenol (0.700 mg, 33 mmol) and 3 equivalents of cesium carbonate in 6.0 ml of DMF. The mixture was stirred at RT for 10 minutes. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (1 g, 26 mmol), the reaction vessels were capped and irradiated at 150° C. for 15 min in the microwave, at which time the reaction was determined complete by LCMS. The mixture was allowed to cool to ambient temperature and material from the five vessels was combined. A deep brown solid crashed out with addition of water. Filtered solids, washed with water and dried overnight in the vacuum oven to afford 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as a brown solid.

Workup

  1. customthe reaction vessels
  2. customwere capped
  3. customirradiated at 150° C. for 15 min in the microwave, at which time the reaction
  4. temperatureto cool to ambient temperature
  5. filtrationFiltered solids
  6. washwashed with water
  7. customdried overnight in the vacuum oven

Sources & evidence

ORD record
ord-3a36415fbf3f4f1eba0dc4dc2065b90a
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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