Ethanol → HCID 21834282, compound

HRID 918202Notes

Reaction equation

HRID 918202 reaction equation
[OH-].[K+].C(O)C.[NH2:6][C:7]1[CH:8]=[C:9]([OH:16])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14].Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>O>[N:21]1[CH:22]=[CH:23][C:18]([O:16][C:9]2[CH:10]=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:7]([CH:8]=2)[NH2:6])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 122884-ChloropyridineHCID 14797Potassium HydroxideHCID 1675273-Amino-4-nitrophenol

Product 1

HCID 21834282HCID 21834282, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 0.1 m. of potassium hydroxide in water is added to an ethanol (100 ml.)-water (175 ml.) mixture containing 15.4 g. (0.1 m.) of 3-amino-4-nitrophenol. The mixture is then heated to 50°C. at which point a solution of 0.1 m. of 4-chloropyridine in 75 ml. of ethanol is added dropwise over a 45 minute period. Then the mixture is heated at reflux for 18 hours, cooled and worked up to give a crystalline yellow solid, m.p. 170°-175°C. of 5-(4-pyridyloxy)-2-nitroaniline.

Workup

  1. additioncontaining 15.4 g
  2. temperatureThen the mixture is heated
  3. temperatureat reflux for 18 hours
  4. temperaturecooled

Sources & evidence

ORD record
ord-9d60eaec747b4d358d1b05c35ac449e0
Source dataset
uspto-grants-1976_07
Patent number
US03969526

Reaction notes

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