Potassium Hydroxide → 4-(Pyridin-2-ylmethoxy)aniline

HRID 1975737Notes

Reaction equation

HRID 1975737 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[K+]>C(O)C>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19098335N-acetyl-4-(pyrid-2-ylmethoxy)aniline

Product 1

HCID 104427734-(Pyridin-2-ylmethoxy)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-acetyl-4-(pyrid-2-ylmethoxy)aniline (116 g; 480 mmol), prepared as in step 1, in 1000 mL 95% ethanol and 130 mL 10M aqueous KOH was refluxed for 2 days. The reaction was concentrated and diluted with water. The mixture was extracted with ethyl acetate. The extracts were dried over magnesium sulfate and concentrated to give 4-(pyrid-2-ylmethoxy)aniline as a brown oil.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-981d6e0103a24384920d019ea54fc202
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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