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

HRID 1590714Notes

Reaction equation

HRID 1590714 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-yl-methoxy)aniline (Step A, 108.9 g) in 1 L 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-2199548498b2459f9c03147b65108c6b
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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