Pyridine → ID-8

HRID 1075657Notes

Reaction equation

HRID 1075657 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13](C(C)C)=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=3[C:10]([N+:21]([O-:23])=[O:22])=[C:9]2/[CH:24]=C/N(C)C)=[CH:4][CH:3]=1.S(C1C=CC=CC=1[C:35](OC(=O)C1C=CC=CC=1S(O)(=O)=O)=[O:36])(O)(=O)=O.N1C=CC=CC=1>C1(C)C=CC=CC=1.[OH-].[Na+].CO>[CH3:24][C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([O:36][CH3:35])=[CH:3][CH:4]=2)[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[C:10]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 3

HCID 1049PyridineHCID 13795534Sulphobenzoic anhydrideHCID 102516351HCID 102516351, compound

Product 1

HCID 791637ID-8Yield 54%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

23.6 g of ID-1 were refluxed together with 20.2 g of sulphobenzoic anhydride and 9 ml of pyridine in 200 ml of toluene. The oil formed was taken up in 300 ml of NaOH 1N and again heated to reflux with 200 ml of toluene. After elimination of the solvents by evaporation the precipitate formed was taken up in 500 ml of methanol. The precipitate, a lightly yellow powder, dissolved but recrystallized immediately. The yield was 54%.

Workup

  1. customThe oil formed
  2. temperatureagain heated
  3. customAfter elimination of the solvents by evaporation the precipitate
  4. customformed
  5. dissolutionThe precipitate, a lightly yellow powder, dissolved
  6. customrecrystallized immediately

Sources & evidence

ORD record
ord-0ea0bb87c0f34cea8d9d79d61e1629df
Source dataset
uspto-grants-1999_05
Patent number
US05905166

Reaction notes

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