Pyridine → HCID 23678692, compound

HRID 990315Notes

Reaction equation

HRID 990315 reaction equation
[NH2:1][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.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C[O-].[Na+:31]>CO>[Na+:31].[C:22]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([O-:15])(=[O:13])=[O:14])=[CH:9]2)=[CH:4][CH:3]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 681247-Aminonaphthalene-2-sulfonic acid2×HCID 10942334Sodium Methoxide

Product 1

HCID 23678692HCID 23678692, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3.75 g (16.8 mmol) of 7-amino-naphthalene-2-sulfonic acid (compound 1) was added 20 mL each of pyridine and acetic anhydride. The reaction was allowed to stir at ambient temperature for 24 hours. The black reaction was cooled in an ice bath and then 45 mL of methanol was added slowly. After 1 hour, a solution of sodium methoxide (425 mg of sodium in 10 mL methanol) was added. A precipitate formed. The suspension was allowed to stir for 2 hours and then the solid was collected by vacuum filtration and was washed with ethyl acetate. This provided 4.4 g of compound 130.

Workup

  1. customThe black reaction
  2. temperaturewas cooled in an ice bath
  3. waitAfter 1 hour
  4. customA precipitate formed
  5. stirringto stir for 2 hours
  6. filtrationthe solid was collected by vacuum filtration
  7. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-e1e269b4c217453d92a9bcf5df1ba029
Source dataset
uspto-grants-2002_10
Patent number
US06458998B1

Reaction notes

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