Ammonia → 4-[(Pyridin-4-yl)amino]phenol

HRID 266757

Reaction equation

HRID 266757 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.N>Br>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3628677N-(4-methoxyphenyl)pyridin-4-amine

Product 1

HCID 130984564-[(Pyridin-4-yl)amino]phenol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of the product from step (i) above (2.0 g) and 48% w/v hydrobromic acid (30 ml) was heated at 140° C. for 4 hours. The cooled solution was neutralised with 0.880 ammonia solution and then extracted four times with ethyl acetate. The combined organic extracts were washed with water and saturated sodium chloride solution, then dried (MgSO4) and evaporated. Purification by flash chromatography on silica, eluting with 10 to 20% v/v methanol/dichloromethane gave 4-(4-pyridylamino)phenol, 0.78 g as an off-white solid: m.p. 246°-248° C.; NMR (CDCl3 +d6DMSO) δ 8.92 (1H, b), 8.09 (2H, d), 7.31 (1H, s), 7.00 (2H, d), 6.79 (2H, d), 6.67 (2H, dd); m/e 187 (M+H)+.

Workup

  1. extractionextracted four times with ethyl acetate
  2. washThe combined organic extracts were washed with water and saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica
  6. washeluting with 10 to 20% v/v methanol/dichloromethane

Sources & evidence

ORD record
ord-a737062066b54e3481095b72f2073ca3
Source dataset
uspto-grants-1997_07
Patent number
US05652242

Linked notes

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