Sodium Hydroxide → 2-(4-Hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-1-methylquinazolin

HRID 336736ノート

反応式

HRID 336736 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=O)[N:6]=[C:7]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([O:23]C(=O)C)=[C:18]([CH3:27])[CH:17]=1)[N:8]2[CH3:15].[OH-].[Na+]>C(O)C>[OH:23][C:19]1[C:20]([CH3:22])=[CH:21][C:16]([CH:7]2[N:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:3]=3[O:2][CH3:1])[N:8]2[CH3:15])=[CH:17][C:18]=1[CH3:27]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 66661452Acetic acid 4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinazolin-2-yl)-2,6-dimethyl-phenyl ester

生成物 1

HCID 866612712-(4-Hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-1-methylquinazolin収率 44.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2,4-dimethoxy-6-methylamino-benzamide (0.28 g, 1.33 mmol) in pyridine (10 mL) was added to acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester (1.1 eq.) and stirred at room temperature for 14 h. The solvent was removed and the reaction mixture was acidified with 1 N HCl and extracted with ethyl acetate. The solvent was removed and the crude was purified by silica gel column chromatography (40 g) employing 1% methanol in dichloromethane to give acetic acid 4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenyl ester (0.34 g, 67%). Acetic acid 4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenyl ester (0.34 g, 0.89 mmol) was dissolved in ethanol (5 mL), 5% aqueous NaOH solution (10 mL) was added dropwise and the mixture was stirred at room temperature for 1.5 h. The compound was extracted with ethyl acetate and washed with ether to give 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-1-methylquinazolin-4(1H-one (0.13 g, 43%). Selected data: MS (ES) m/z: 340.17; MP 188.5-189.1° C.

後処理

  1. extractionThe compound was extracted with ethyl acetate
  2. washwashed with ether

出典と根拠

ORDレコード
ord-eb7652a6711f4c0a80852e09c4f96cb7
出典データセット
uspto-grants-2014_11
特許番号
US08889698B2

反応ノート

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