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Nitric Acid → 4-(2-Methylamino-pyrimidin-4-yloxy)-2-nitro-phenol

HRID 491660
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HRID 491660 반응식
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[N+:17]([O-])([OH:19])=[O:18].C([O-])(O)=O.[Na+]>CC(O)=O.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:6]=[CH:5][N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 177565984-(2-Methylamino-pyrimidin-4-yloxy)-phenol

생성물 1

HCID 177550144-(2-Methylamino-pyrimidin-4-yloxy)-2-nitro-phenol

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

4-(2-Methylamino-pyrimidin-4-yloxy)-phenol (Step C, 0.20 g, 0.92 mmol) was dissolved in 5 mL AcOH at RT. Fuming HNO3 (0.064 g, 0.92 mmol) was diluted with about 0.012 mL water, then added dropwise over 1 min to the reaction. The reaction was stirred for 18 h, after which it was added slowly to 40 mL saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography using hexanes/EtOAc gradient to yield the title compound. MS (MH+)=263.1; Calc'd 262.23 for C11H10N4O4.

후처리

  1. additionadded dropwise over 1 min to the reaction
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-860a34310c3c4f4bafee8a4b3b21e69e
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531553B2

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