Sulfuric Acid → 2-Nitro-6-(phenylaminocarbonyl)phenol

HRID 1419417

반응식

HRID 1419417 반응식
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:17]([O-])([O-:19])=[O:18].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[C:11]=1[OH:16])([O-:19])=[O:18]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 6872SalicylanilideHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

생성물 1

HCID 185513542-Nitro-6-(phenylaminocarbonyl)phenol수율 42.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2-Phenylaminocarbonylphenol (5.00 g, 23 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (2.20 g, 25.5 mmol). The addition of sulfuric acid (3 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(2.50 g, 42%). 1H NMR (CD3COCD3): δ 8.15 (d, 1H), 8.09 (d, 1H), 7.51 (d, 1H), 7.30 (d, 1H), 7.10 (t, 1H), 7.01 (t, 1H).

후처리

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-939b99ed7c4b4277ad7857525fd9987d
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886044

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