Methyl 4-methoxyacetoacetate → HCID 178496286、化合物

HRID 1624650

反応式

HRID 1624650 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:3]=1[NH2:4].[N:10]([O-])=O.[Na+].[CH3:14][O:15][CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20].CC([O-])=O.[Na+]>Cl.O.CCO>[F:1][C:2]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:3]=1[NH:4][N:10]=[C:18]([C:17](=[O:23])[CH2:16][O:15][CH3:14])[C:19]([O:21][CH3:22])=[O:20]

参加物

8

反応物 4

HCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 254184602-Fluoro-5-iodoaniline

生成物 1

HCID 178496286HCID 178496286、化合物収率 87%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 2-fluoro-5-iodoaniline (9.83 g, 41.5 mmol) in 6 M HCl aqueous solution (83.0 mL) was added a solution of NaNO2 (3.43 g, 49.8 mmol) in water (8.3 mL) at 0° C. To a suspension of methyl 4-methoxy-3-oxobutanoate (5.37 mL, 41.5 mmol) and NaOAc (124 g) in EtOH (70 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 10 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (14.2 g, 87% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.31 (3H, s), 3.83 (3H, s), 4.64 (2H, s), 7.03-7.41 (1H, m), 7.43-7.66 (1H, m), 7.85-8.07 (1H, m), 12.20 (1H, brs).

後処理

  1. additionwas added the above solution at 0° C
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6142beb941634b0a97b92eec75fc9b5f
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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