4-Aminophenol → 4-(5-Methylpyridin-2-ylamino)phenol

HRID 473712Notes

Reaction equation

HRID 473712 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1.C([O-])(O)=O.[Na+]>O>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 516892Sodium BicarbonateHCID 5813932-Chloro-5-methyl-pyridine

Product 1

HCID 593739864-(5-Methylpyridin-2-ylamino)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-aminophenol (2 g, 18.33 mmol) and 2-chloro-5-methylpyridine (2.57 g, 20.16 mmol) was heated neat at 180° C. in 2 h. The reaction mixture was cooled, taken up in H2O, neutralized with saturated NaHCO3, extracted with DCM (3×). The extracts were dried over MgSO4, concentrated to give the dark purple solid. MS (ESI, pos. ion) m/z: 201.1 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM (3×)
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customto give the dark purple solid

Sources & evidence

ORD record
ord-e3015e5419014714beac64afa1bf1bdc
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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