Acetic Anhydride → HCID 89657260, 화합물

HRID 1056944노트

반응식

HRID 1056944 반응식
[NH2:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:24](OCCCCC)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:9][C:6]1[C:7]2[CH:8]=[N:24][NH:1][C:2]=2[C:3](=[O:11])[N:4]([CH3:10])[CH:5]=1

참가 물질

7

반응물 4

HCID 7918Acetic AnhydrideHCID 10026Pentyl nitriteHCID 517044Potassium AcetateHCID 896563843-Amino-5-bromo-1,4-dimethyl-2(1H)-pyridinone

생성물 1

HCID 89657260HCID 89657260, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-amino-5-bromo-1,4-dimethylpyridin-2(1H)-one (12.1 g, 55.9 mmol) in toluene (300 mL) was treated with acetic anhydride (15.8 mL, 168 mmol) followed by potassium acetate (6.58 g, 67.1 mmol) and stirred at RT overnight. The reaction mixture was treated with amyl nitrite (11.3 mL, 83.8 mmol) and heated at 80° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried with magnesium sulfate, filtered, and concentrated to give a mixture of the desired product along with the acetylated desired product. This mixture was diluted with methanol (490 mL) and treated with 1.0 M sodium hydroxide in water (280 mL) and stirred at RT for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried with magnesium sulfate, filtered, and concentrated to give crude product. Purification by flash column chromatography (100% hexanes to 100% EtOAc) gave the desired product (8.4 g, 66%). LCMS calculated for C7H7BrN3O (M+H)+: m/z=228.0, 230.0. found: 227.9, 229.9.

후처리

  1. temperatureheated at 80° C. overnight
  2. washwashed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give

출처 및 근거

ORD 기록
ord-8c0bb9568aef43329e090e80562c8f53
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399640B2

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