Sulfuric Acid → 6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-5-one

HRID 1733968Notes

Reaction equation

HRID 1733968 reaction equation
CC1C=CC(S([N:11]2[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[C:13]3[CH:19]=[CH:20][CH:21]=[N:22][C:12]2=3)(=O)=O)=CC=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[N:22]1[C:12]2[NH:11][CH2:17][CH2:16][CH2:15][C:14](=[O:18])[C:13]=2[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19699054HCID 19699054, compound

Product 1

HCID 196991086,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-5-oneYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5.00 g of 6,7,8,9-tetrahydro-9-[(4-methylphenyl)sulfonyl]-5H-pyrido[2,3-b]azepin-5-one in 60 ml of 40% (v/v) sulfuric acid in acetic acid is heated at 60° C. for 11 hours. The mixture is chilled and poured into 350 ml of ice water (cooled in an ice bath) with thorough stirring. To the cold mixture is added solid NaOH until the pH is 8 while keeping the temperature below 30° C. The mixture is filtered and the solid washed with ethyl acetate. The organic layer of the filtrate is separated and the aqueous layer extracted with ethyl acetate. The organic layer and extracts are combined and treated with activated carbon. The mixture is filtered through MgSO4 and the solvent removed under vacuum to give 2.0 g of yellow crystals.

Workup

  1. temperatureThe mixture is chilled
  2. customthe temperature below 30° C
  3. filtrationThe mixture is filtered
  4. washthe solid washed with ethyl acetate
  5. customThe organic layer of the filtrate is separated
  6. extractionthe aqueous layer extracted with ethyl acetate
  7. additiontreated with activated carbon
  8. filtrationThe mixture is filtered through MgSO4
  9. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-6f2b7face1a649618709d7eec34691ff
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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