Hydrogen Peroxide → Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate

HRID 906181노트

반응식

HRID 906181 반응식
[NH2:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].OO.C(=O)([O-])[O-:18].[K+].[K+]>CS(C)=O>[NH2:1][C:2]1[C:3]([C:13]([NH2:14])=[O:18])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67402842Methyl 5-amino-4-cyano-2-methylbenzoate

생성물 1

HCID 67403771Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate수율 208%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Methyl 5-amino-4-cyano-2-methylbenzoate (151 mg, 0.79 mmol) (synthesized according to reagent preparation 41) was dissolved in DMSO (1.5 mL). 30% Aqueous hydrogen peroxide (0.3 mL) and potassium carbonate (35 mg, 0.25 mmol) were added, and the mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted (2×) with ethyl acetate. The combined organic portion was dried over sodium sulfate, filtered and concentrated to a yellow oil which was purified by preparative reverse phase HPLC to afford methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate (108 mg, 0.52 mmol, 66% yield). NMR (400 MHz, CDCl3): δ 7.85 (s, 1H), 7.45 (br s, 1H), 7.26 (s, 1H), 7.19 (br s, 1H), 6.48 (s, 2H), 3.80 (s, 3H), 2.32 (s, 3H); MS (EI) for C10H12N2O3: 209 (MH+).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous portion was extracted (2×) with ethyl acetate
  3. dry with materialThe combined organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil which
  6. customwas purified by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-681ce2a519fd405591d2cd681d47038d
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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