5-Amino-2-methylphenol → HCID 10291467, compound

HRID 1934970Notes

Reaction equation

HRID 1934970 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:12][CH2:13][CH3:14])[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-])(O)=O.[Na+]>C(O)C>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:15][CH3:16])[N:5]=[CH:4][C:3]([C:17]#[N:18])=[C:2]2[NH:23][C:22]1[CH:24]=[CH:25][C:26]([CH3:27])=[C:20]([OH:19])[CH:21]=1)[CH3:14]

Participants

5

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 10539447HCID 10539447, compound

Product 1

HCID 10291467HCID 10291467, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.00 g (3.82 mmol) of 4-chloro-6-ethoxy-7-methoxyquinoline-3-carbonitrile and 0.563 g (4.58 mmol) of 3-hydroxy-4-methylaniline in 20 mL of ethanol was refluxed under N2 for 8 h. Saturated NaHCO3 was added, volatile material was removed and the residue was azeotroped with ethanol. The crude product was slurried with hexane, filtered, washed with water and cold ethanol and dried. Recrystallization from ethanol gave 0.632 g of 6-ethoxy-4-(3-hydroxy-4-methylphenylamino)-7-methoxyquinoline-3-carbonitrile as light yellow crystals: mass spectrum (electrospray, m/e): M+H 349.9.

Workup

  1. temperaturewas refluxed under N2 for 8 h
  2. customvolatile material was removed
  3. customthe residue was azeotroped with ethanol
  4. filtrationfiltered
  5. washwashed with water and cold ethanol
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-d14426ba35ea415d98612212b4532ea6
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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