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

HRID 1588430Notes

Reaction equation

HRID 1588430 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>CCO>[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 1, 108.9 g) in 1 L of 95% EtOH 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 EtOH was partially removed under vacuum. The mixture was then diluted with H2O (200 mL) and the fine off-white crystals were collected and thoroughly rinsed with water. The material, after air-drying, yielded 4-(quinolin-2-ylmethoxy)aniline 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. customEtOH was partially removed under vacuum
  6. additionThe mixture was then diluted with H2O (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-b73229b782fd443f82bfedca8de43f9a
Source dataset
uspto-grants-1993_06
Patent number
US05221678

Reaction notes

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