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

HRID 1385413Notes

Reaction equation

HRID 1385413 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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 (30 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/CH2CH2) gave the desired product (2.50 g, 42%). 1H NMR (CD3COCD3): d 8.15 (d, 1H), 8.09 (d, 1H), 7.51 (d, 1H), 7.30 (d, 1H), 7.10 (t, 1H), 7.01 (t, 1H).

Workup

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

Sources & evidence

ORD record
ord-f40847689a234954b59e897064f78743
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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