Potassium nitrosodisulfonate → HCID 14257810, compound

HRID 1165899Notes

Reaction equation

HRID 1165899 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[C:7]([CH3:20])[C:6]=2[CH:5]=[C:4]([CH3:21])[C:3]=1[CH3:22].N(S([O-])(=O)=O)(S([O-])(=O)=[O:26])[O].[K+].[K+]>CC(C)=O.OP([O-])(O)=O.[K+]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:8]2[O:9][C:10]3[C:2](=[O:1])[C:3]([CH3:22])=[C:4]([CH3:21])[C:5](=[O:26])[C:6]=3[C:7]=2[CH3:20])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 3032624Potassium nitrosodisulfonateHCID 14257799HCID 14257799, compound

Product 1

HCID 14257810HCID 14257810, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516951Monobasic potassium phosphateSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 7-hydroxy-2-(4-methoxybenzyl)-3,5,6-trimethylbenzofuran from Step 4 (8.6g, 29 mmol) in acetone (1.5 L) was added rapidly to a solution of potassium nitrosodisulfonate (Fremy's salt) (25 g, 93 mmol) in 0.055M KH2PO4 buffer (1.5 L) at room temperature. The reaction was slowly heated to 45° C. over a period of 2 hr. The reaction was then cooled and the quinoline was extracted with EtOAc (2x, 500 mL). Evaporation of the organic solvent gave a solid residue which was crystallized and re-crystallized from EtOH, to give the title compound, mp 111°-113° C.

Workup

  1. temperatureThe reaction was then cooled
  2. extractionthe quinoline was extracted with EtOAc (2x, 500 mL)
  3. customEvaporation of the organic solvent
  4. customgave a solid residue which
  5. customwas crystallized
  6. customre-crystallized from EtOH

Sources & evidence

ORD record
ord-cde8199a2af6485d898ab4c902ff1eaa
Source dataset
uspto-grants-1990_03
Patent number
US04912131

Reaction notes

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