5-Amino-2-methylphenol → 7-Benzyloxy-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline hydrochloride

HRID 393607Notes

Reaction equation

HRID 393607 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Cl.[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([Cl:29])=[CH:24][CH:25]=[N:26]2)=[CH:21][C:20]=1[O:30][CH3:31])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCCO)C>[ClH:29].[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([NH:5][C:4]3[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([OH:1])[CH:3]=3)=[CH:24][CH:25]=[N:26]2)=[CH:21][C:20]=1[O:30][CH3:31])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 226465617-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride

Product 1

HCID 226466137-Benzyloxy-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline hydrochlorideYield 61.5%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 3-hydroxy-4-methylaniline (68 mg, 0.55 mmol) and 7-benzyloxy-4-chloro-6-methoxyquinoline hydrochloride (168 mg, 0.5 mmol), (prepared as described for the starting material in Example 3), in 2-ethoxyethanol (5 ml) was heated at reflux for 1 hour. The mixture was allowed to cool, the precipitate collected by filtration, washed with 2-ethoxyethanol and then ether and dried under vacuum to give 7-benzyloxy-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline hydrochloride (130 mg, 61%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. filtrationthe precipitate collected by filtration
  5. washwashed with 2-ethoxyethanol
  6. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-07d404dbdd944089afcd2433765768df
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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