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

HRID 1353657노트

반응식

HRID 1353657 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 6104125-Methyl-3-phenyl-1H-indazole수율 80.4%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-43ef8e8416bb4a8391589c6e7a6ef082
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220771B2

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