5-Amino-2-methylphenol → 4-(3-Hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

HRID 393602Notes

Reaction equation

HRID 393602 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]([O:13][CH3:14])[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]>CN(C=O)C.C(O)(C)C>[ClH:2].[OH:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[CH3:28])[NH:24][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 226466534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

Product 1

HCID 226466604-(3-Hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochlorideYield 58%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (250 mg, 0.82 mmol) and 3-hydroxy-4-methylaniline (123 mg, 1 mmol) in DMF (5 ml) was heated at 150° C. for 30 minutes. The mixture was diluted with isopropanol and the resulting solid collected by filtration and washed with isopropanol to give 4-(3-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (168 mg, 58%).

Workup

  1. filtrationthe resulting solid collected by filtration
  2. washwashed with isopropanol

Sources & evidence

ORD record
ord-2adbf1d78f3547b083dffdd3c11b2f8a
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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