Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

HRID 5371

反応式

HRID 5371 の反応式
[H-].[Na+].[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([NH2:13])=[CH:8][C:7]=1[OH:14].[CH3:16][O:17][CH2:18][CH2:19]Br.O>CN(C)C=O>[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([NH2:13])=[CH:8][C:7]=1[O:14][CH2:19][CH2:18][O:17][CH3:16]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoate

生成物 1

HCID 539320764-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 60% sodium hydride/oil dispersion (1.00 g, 25 mmol) in anhydrous dimethylformamide (40 mL) under nitrogen was treated with 4-amino-5-chloro-2-hydroxybenzoic acid methyl ester (4.03 g, 20 mmol), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 25 mmol). The mixture was heated to 95°±5° C. for 1.5 hours, then cooled and added to water (250 mL). The aqueous suspension was filtered, and the solid was washed with water, air dried, collected, and recrystallized from ether/hexane to afford 2.75 g (53%) of the title compound; mp 121.0°-122.5° C.

後処理

  1. temperatureThe mixture was heated to 95°±5° C. for 1.5 hours
  2. temperaturecooled
  3. filtrationThe aqueous suspension was filtered
  4. washthe solid was washed with water, air
  5. customdried
  6. customcollected
  7. customrecrystallized from ether/hexane

出典と根拠

ORDレコード
ord-4901bf8f54dc48a7ac09c0ddf6fdf741
出典データセット
uspto-grants-1993_09
特許番号
US05244907

関連ノート

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