Acetic Anhydride → 1H-Indazole-4-carboxylic acid, 1-acetyl-6-bromo-, methyl ester

HRID 1854103노트

반응식

HRID 1854103 반응식
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14]([O-:17])(=O)[CH3:15].[K+].C(OC(=O)C)(=O)C.[N:26](OC(C)(C)C)=O.C1OCCOCCOCCOCCOCCOC1>C(Cl)(Cl)Cl>[C:14]([N:1]1[C:2]2[CH:11]=[C:10]([Br:12])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=2[CH:13]=[N:26]1)(=[O:17])[CH3:15]

참가 물질

7

반응물 5

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

생성물 1

HCID 682954331H-Indazole-4-carboxylic acid, 1-acetyl-6-bromo-, methyl ester수율 98.5%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 61.5 mmol) in chloroform (150 mL), was added potassium acetate (6.32 g, 64.4 mmol) and acetic anhydride (12.6 g, 122.9 mmol) and reaction mixture was stirred at room temperature for 12 h. After this time, tert-butyl nitrite (25.3 g, 246.1 mmol) and 18-crown-6 (5.7 g, 21.5 mmol) were added and reaction stirred again at 65° C. for 3 h. On completion, the reaction mass was cooled to room temperature, diluted with chloroform (500 mL) and washed with sat. sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford the title compound (18 g, 98.3%).

후처리

  1. customreaction
  2. stirringstirred again at 65° C. for 3 h
  3. temperatureOn completion, the reaction mass was cooled to room temperature
  4. washwashed with sat. sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4f002414fc664016a372f82af4da6be1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962620B2

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