5-Amino-2-methylphenol → HCID 22646537, compound

HRID 393650Notes

Reaction equation

HRID 393650 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([C:13]#[N:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[OH:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[CH3:28])[NH2:24]>C(O)(C)C>[ClH:2].[C:13]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:15][CH2:16][CH2:17][O:18][CH3:19])[N:6]=[CH:5][CH:4]=[C:3]2[NH:24][C:23]1[CH:25]=[CH:26][C:27]([CH3:28])=[C:21]([OH:20])[CH:22]=1)#[N:14]

Participants

4

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 22646521HCID 22646521, compound

Product 1

HCID 22646537HCID 22646537, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-cyano-7-(2-methoxyethoxy)quinoline hydrochloride (220 mg 0.84 mmol), (prepared as described for the starting material in Example 1), and 3-hydroxy-4-methylaniline (123 mg, 1 mmol) in isopropanol (10 ml) was heated at reflux for 1 hour. The mixture was allowed to cool, the solid product was collected by filtration, washed with acetone and dried to give 6-cyano-4-(3-hydroxy-4-methylanilino)-7-(2-methoxyethoxy)quinoline hydrochloride (210 mg, 60%) as an orange solid.

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 1 hour
  4. temperatureto cool
  5. filtrationthe solid product was collected by filtration
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-a2bef354b557403e8c9c6dc97972b0c9
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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