5-Amino-2-methylphenol → 7-Ethoxy-4-[(3-hydroxy-4-methylphenyl)amino]-6-methoxy-3-quinolinecarbonitrile

HRID 1935029Notes

Reaction equation

HRID 1935029 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH3:16])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[OH:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[CH3:27])[NH2:23]>C(O)C>[CH2:15]([O:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:23][C:22]3[CH:24]=[CH:25][C:26]([CH3:27])=[C:20]([OH:19])[CH:21]=3)=[C:3]([C:17]#[N:18])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:12][CH3:13])[CH3:16]

Participants

4

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 224667527-Ethoxy-4-[(3-hydroxy-4-methylphenyl)amino]-6-methoxy-3-quinolinecarbonitrileYield 54.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 500 mg (1.90 mmol) 4-chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile, 30 ml ethanol, and 281 mg (2.28 mmol) 3-hydroxy-4-methylaniline was heated to reflux under N2 overnight. Removed heat and made basic with saturated sodium bicarbonate. Stripped solvents and slurried residue in hexane. Collected solids, washed with water, and dried in vacuo, giving 364 mg off-white solid: mass spectrum (electrospray m/e): M+H=349.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 overnight
  3. customRemoved
  4. temperatureheat
  5. customCollected solids
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-bd05f2147d684ddf839861e482305a6f
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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