Hydrochloric Acid → methyl 2-[(4-bromo-2,5-difluorophenyl)hydrazinylidene]-4-methoxy-3-oxobutanoate

HRID 1624692

反応式

HRID 1624692 の反応式
[N:1]([O-])=O.[Na+].[Br:5][C:6]1[C:12]([F:13])=[CH:11][C:9]([NH2:10])=[C:8]([F:14])[CH:7]=1.Cl.[CH3:16][O:17][CH2:18][C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22].CC([O-])=O.[Na+]>O.CO>[Br:5][C:6]1[C:12]([F:13])=[CH:11][C:9]([NH:10][N:1]=[C:20]([C:19](=[O:25])[CH2:18][O:17][CH3:16])[C:21]([O:23][CH3:24])=[O:22])=[C:8]([F:14])[CH:7]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 27732854-Bromo-2,5-difluoroanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 178496284methyl 2-[(4-bromo-2,5-difluorophenyl)hydrazinylidene]-4-methoxy-3-oxobutanoate収率 105.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A solution of NaNO2 (7.9 g, 115 mmol) in H2O (20 mL) was added dropwise at 0° C. to a mixture of 4-bromo-2,5-difluoroaniline (20 g, 96 mmol) and 6 M HCl aqueous solution (96 mL, 576 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (12.4 mL, 96 mmol) and NaOAc (34 g, 576 mmol) in MeOH (165 mL) pre-cooled at 0° C. The precipitate was collected by filtration, washed with water and dried at room temperature to give the title compound (37 g, 100% yield) as a red solid: 1H NMR (300 MHz, DMSO-d6): δ ppm 3.34 (3H, s), 3.83 (3H, s), 4.68 (2H, s), 7.70 (1H, dd, J=9.7, 7.0 Hz), 7.89 (1H, dd, J=10.6, 6.1 Hz), 12.16 (1H, s).

後処理

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried at room temperature

出典と根拠

ORDレコード
ord-b92395b0d8ca4c4294d289e454875add
出典データセット
uspto-grants-2014_07
特許番号
US08778944B2

関連ノート

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