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

HRID 1656336Notes

Reaction equation

HRID 1656336 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 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, yielding 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-10703ce3931240db975c3b7ddd1b8056
Source dataset
uspto-grants-1993_10
Patent number
US05254541

Reaction notes

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