Hydrochloric Acid → HCID 178496282、化合物

HRID 1895155ノート

反応式

HRID 1895155 の反応式
[N:1]([O-])=O.[Na+].[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH3:22][O:23][CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28].CC([O-])=O.[Na+]>O.CO>[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][N:1]=[C:26]([C:25](=[O:31])[CH2:24][O:23][CH3:22])[C:27]([O:29][CH3:30])=[O:28])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 114998094-(Benzyloxy)-2-fluoroanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 178496282HCID 178496282、化合物収率 94.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of NaNO2 (2.07 g, 30 mmol) in H2O (5 mL) was added dropwise at 0° C. to a mixture of 4-(benzyloxy)-2-fluoroaniline (5.43 g, 25 mmol) and 6 M HCl aqueous solution (25 mL, 150 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (3.24 mL, 24 mmol) and NaOAc (12.3 g, 150 mmol) in MeOH (50 mL) pre-cooled at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (8.48 g, 91% yield) as a yellow solid: 1H NMR (300 MHz, CDCl3): δ ppm 3.500 (3H×0.46, s), 3.502 (3H×0.54, s), 3.88 (3H×0.54, s), 3.92 (3H×0.46, s), 4.65 (2H×0.46, s), 4.68 (2H×0.54, s), 5.06 (2H×0.54, s), 5.07 (2H×0.46, s), 6.75-6.86 (2H, m), 7.32-7.44 (5H, m), 7.53 (1H×0.46, t, J=9.0 Hz), 7.76 (1H×0.54, t, J=9.0 Hz), 13.12 (1H×0.46, brs), 15.13 (1H×0.54, brs).

後処理

  1. extractionextracted with AcOEt
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/AcOEt

出典と根拠

ORDレコード
ord-bad748f5352c4c49998effbb0ef53344
出典データセット
uspto-grants-2013_08
特許番号
US08513251B2

反応ノート

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