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Hydrogen Bromide → 3-(2-Oxoacetyl)benzoic acid

HRID 498244
ノート
印刷プレビュー

反応式

HRID 498244 の反応式
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:15]=[N:14][C:13]([CH3:16])=[N:12][CH:11]=2)[CH:5]=1.Br[CH2:19][C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26])=[O:21].Br>CS(C)=O>[C:4]([O:27][C:25](=[O:26])[CH2:24][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:15]=[N:14][C:13]([CH3:16])=[N:12][CH:11]=2)[CH:5]=1)=[O:17])([CH3:9])([CH3:5])[CH3:3].[O:2]=[CH:19][C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26])=[O:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 260Hydrogen BromideHCID 27568353-(Bromoacetyl)benzoic acidHCID 694894533-(3-Methyl-[1,2,4]triazin-6-yl)-benzoic acid methyl ester

生成物 2

HCID 223179033-(2-Oxoacetyl)benzoic acidHCID 694865703-[3-(3-Methyl-[1,2,4]triazin-6-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

反応条件

温度
55 °C

実験手順

The title compound was prepared from 3-(3-methyl-[1,2,4]triazin-6-yl)-benzoic acid methyl ester [prepared by the following procedure: To a solution of 3-bromoacetyl-benzoic acid (2.43 g, 10 mmol) in DMSO (17 ml) was added 48% aqueous HBr (3.4 ml) and the mixture was stirred at 55° C. for 0.5 h. The cooled mixture was partitioned between AcOEt and H2O, the organic layer was washed with brine, dried and evaporated in vacuum and the solid residue was triturated with Et2O/hexane to give 3-oxoacetyl-benzoic acid (1.08 g) as a white solid. A solution of this material (3.92 g, 20 mmol) and acetyl hydrazide (1.63 g, 22 mmol) in MeOH (20 ml) was stirred at RT for 1 h. The mixture was evaporated in vacuum and the residue was heated in an autoclave in 5N NH3-MeOH (30 ml) at 150° C. for 3 h. The mixture was cooled and partitionned between AcOEt and sat. NaHCO3-solution. The aqueous phase was acidified to pH 3with 3N HCl and extracted with AcOEt. The crude product obtained from the AcOEt extract was esterified by heating in 1N HCl-MeOH (80 ml) for 18 h at 50° C. and the crude ester obtained was purified by chromatography (silica gel, AcOEt) to give the methyl ester as light-yellow solid (0.45 g).] (0.8 g, 3.5 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a yellow solid (1.34 g, crude product).

後処理

  1. customprepared by the following procedure
  2. customThe cooled mixture was partitioned between AcOEt and H2O
  3. washthe organic layer was washed with brine
  4. customdried
  5. customevaporated in vacuum
  6. customthe solid residue was triturated with Et2O/hexane

出典と根拠

ORDレコード
ord-51ccac3027534fedbf6cdec28c3a1c81
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949542B2

反応ノート

読み込み中…

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