Lithium hydroxide, monohydrate → 2-Bromo-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acid

HRID 393041ノート

反応式

HRID 393041 の反応式
O.[OH-].[Li+].[Br:4][C:5]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8]>O.O1CCCC1.CO>[Br:4][C:5]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 235607712-Bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoic acid methyl ester

生成物 1

HCID 226613232-Bromo-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acid収率 102.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

A solution of lithium hydroxide monohydrate (4.41 g, 105.1 mmol) in water (15 mL) was added to a solution of 2-bromo-4-[[[(3-hydroxyphenyl)methyl]amino]-carbonyl]benzoic acid, methyl ester (Example 14; 15.30 g, 42.0 mmol) in tetrahydrofuran/methanol (2:1, 21 mL). The solution was stirred at room temperature for 1 h, then it was concentrated to remove tetrahydrofuran and methanol. The remaining aqueous solution was extracted with ethyl acetate (15 mL) and the ethyl acetate extract was discarded. The aqueous layer was acidified with 1 M HCl (75 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (15 mL), dried (MgSO4), filtered, and evaporated to give 2-bromo-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acid (15.1 g, quantitative yield) which was used in the next step without further purification.

後処理

  1. concentrationit was concentrated
  2. customto remove tetrahydrofuran and methanol
  3. extractionThe remaining aqueous solution was extracted with ethyl acetate (15 mL)
  4. extractionthe ethyl acetate extract
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined organic layers were washed with brine (15 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-406adefb281540a6828bd7bc926ecff0
出典データセット
uspto-grants-2004_10
特許番号
US06803384B2

反応ノート

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