4-Aminophenol → HCID 59351255, compound

HRID 473684Notes

Reaction equation

HRID 473684 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH2:9][O:10][CH2:11][CH2:12][CH:13]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:10]1[CH2:11][CH2:12][CH:13]=[C:8]([C:7]2[C:2]([O:21][C:18]3[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=3)=[N:3][CH:4]=[CH:5][N:6]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 59351136HCID 59351136, compound

Product 1

HCID 59351255HCID 59351255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-3-(5,6-dihydro-2H-pyran-3-yl)pyrazine (0.13 g, 0.68 mmol), 4-aminophenol (0.15 g, 1.35 mmol), and cesium carbonate (0.44 g, 1.35 mmol) were mixed in DMF (2 mL) in a microwave tube. The tube was sealed and placed under a nitrogen atmosphere. The reaction mixture was stirred at 120° C. for 2.5 h. The reaction mixture was cooled to room temperature and diluted with water. The resulting precipitate was filtered and washed with water to give 4-(3-(5,6-dihydro-2H-pyran-3-yl)pyrazin-2-yloxy)aniline. MS (ESI, pos. ion) m/z: 270.1 (M+1).

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-d209307fadfd42bdb43bfd1b771aafdb
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

Loading…