Stannous Chloride → 5-Methyl-3-phenyl-1H-indazole

HRID 1353657ノート

反応式

HRID 1353657 の反応式
[C:1]1([C:7]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[NH2:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[CH3:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[NH:16][N:17]=[C:7]2[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 24479Stannous ChlorideHCID 873352-Amino-5-methylbenzophenoneHCID 23668193Sodium Nitrite

生成物 1

HCID 6104125-Methyl-3-phenyl-1H-indazole収率 80.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒

実験手順

To a solution of 2-amino-5-methylphenyl phenyl ketone (2.0 g, 9.5 mmol) in HCl (45 mL of a 6M solution) at 0° C. was added sodium nitrite (NaNO2) (719 mg, 10.4 mmol) in water (2 mL). The reaction was stirred for 30 min when the homogeneous solution was added dropwise to a solution of SnCl2 (5.88, 26 mmol) in concentrated HCl (15 mL) at room temperature. The reaction was stirred for 30 min when it was filtered. The solid was then taken up in ethyl acetate (80 mL) and saturated sodium bicarbonate (80 mL). The suspension was then filtered and the ethyl acetate layer dried (Na2SO4) and concentrated to give the product (1.59 g, 80% yield). (1H NMR (DMSO-d6) δ 7.96 (d, 2H), 7.85 (br s, 1H), 7.54–7.46 (m, 3H), 7.39 (t, 1H), 7.24 (d, 1H), 2.45 (s, 3H); ES-MS (m/z) 209 [M+1]+.

後処理

  1. stirringThe reaction was stirred for 30 min when it
  2. filtrationwas filtered
  3. filtrationThe suspension was then filtered
  4. dry with materialthe ethyl acetate layer dried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-43ef8e8416bb4a8391589c6e7a6ef082
出典データセット
uspto-grants-2007_05
特許番号
US07220771B2

反応ノート

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