Acetamide, N-[4-(2-quinolinylmethoxy)phenyl]- → 4-(Quinolin-2-ylmethoxy)aniline

HRID 1769342Notes

Reaction equation

HRID 1769342 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1)(=O)C>C(O)C>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 2747568Acetamide, N-[4-(2-quinolinylmethoxy)phenyl]-

Product 1

HCID 27475694-(Quinolin-2-ylmethoxy)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-acetyl-4-(quinolin-2-ylmethoxy)aniline (Step A, 108.9 g) in 1L of 95% ethanol containing 10M KOH (120 mL) was heated at reflux under nitrogen in a heating mantle. When the hydrolysis was complete (approx. 36 h), the reaction mixture was cooled and ethanol was partially removed under vacuum. The mixture was then diluted with water (200 mL) and the fine off-white crystals were collected and thoroughly rinsed with water. The material, after air-drying, yielded the title compound which was used as such in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen in a heating mantle
  3. custom(approx. 36 h)
  4. temperaturethe reaction mixture was cooled
  5. customethanol was partially removed under vacuum
  6. additionThe mixture was then diluted with water (200 mL)
  7. customthe fine off-white crystals were collected
  8. washthoroughly rinsed with water
  9. customThe material, after air-drying

Sources & evidence

ORD record
ord-9183f507d79546b3ba5edb1da08497b7
Source dataset
uspto-grants-1995_01
Patent number
US05380850

Reaction notes

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