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

HRID 327223

Reaction equation

HRID 327223 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-ef86d1020e664a9d8a2bf81d9f148297
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Linked notes

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