Ethanol → HCID 86718860, compound

HRID 528797Notes

Reaction equation

HRID 528797 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[Na+].N([O-])=O.[Na+].[Na+].[I-:22].CCO>O.Cl>[I:22][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 5238Sodium IodideHCID 23668193Sodium NitriteHCID 236786932-Naphthalenesulfonic acid, 7-amino-, monosodium salt

Product 1

HCID 86718860HCID 86718860, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of sodium 7-aminonaphthalene-2-sulfonate (Pfaltz and Bauer, 1.00 g, 4.06 mmol) in water (6.0 mL) and conc. HCl (2.0 mL) was cooled to 0° C. A premixed solution of NaNO2 (280 mg, 4.06 mmol) in water (2.0 mL) was added slowly, maintaining the temperature close to 0° C. The reaction mixture was stirred at 0° C. for 1 h. A solution of NaI (609 mg g, 4.06 mmol) in water (3.0 mL) and conc. HCl (1.0 mL) was then added dropwise over 30 min, maintaining a temperature close to 0° C. The reaction mixture was stirred at room temperature for 2 h and then heated to 90° C. for 1 h. The reaction mixture was cooled to room temperature, treated with EtOH (10.0 mL) and concentrated in vacuo. EtOH (10 mL) was added and the mixture was filtered to give the title compound (1.07 g, 79%) as a tan solid. 1H NMR (DMSO-d6) δ 8.45 (s, 1H), 8.09 (s, 1H), 8.76 (d, J=8.6 Hz, 1H), 7.80-7.68 (m, 3H); MS(ESI−) m/z 333.2 (M−H)−.

Workup

  1. temperaturemaintaining the temperature
  2. customclose to 0° C
  3. temperaturemaintaining a temperature
  4. customclose to 0° C
  5. stirringThe reaction mixture was stirred at room temperature for 2 h
  6. temperatureheated to 90° C. for 1 h
  7. temperatureThe reaction mixture was cooled to room temperature
  8. concentrationconcentrated in vacuo
  9. additionEtOH (10 mL) was added
  10. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-fc75e76fa1c6471fb30586bdf50f7c69
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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