Water → 7-Fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 1033382Notes

Reaction equation

HRID 1033382 reaction equation
[N-:1]=[N+]=[N-].[Na+].O.S(=O)(=O)(O)O.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16][CH2:15]2>C(Cl)(Cl)Cl>[F:11][C:12]1[CH:21]=[CH:20][C:19]2[NH:1][C:18](=[O:22])[CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 33557Sodium AzideHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 541064987-Fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-oneYield 11.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium azide 1.1 g (16.92 mmol) was added to a mixture of 6.0 mL of chloroform and 1.1 mL of water at 0° C. Concentrated sulfuric acid (0.44 mL) was added dropwise and the mixture stirred at 0° C. for two hours then filtered. The chloroform layer containing hydrazoic acid was added to a solution of 1.3 g (7.92 mmol) of 6-fluoro-1-tetralone (prepared by the method of Allinger and Jones, J. Org. Chem., 27, 70-76 (1962)) in 4.8 mL of chloroform. Additional sulfuric acid (2.16 mL) was added dropwise with stirring while maintaining the temperature below 40° C. The mixture was stirred at 40° C. for two hours then at room temperature for 16 hours. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was added to ice; the resulting recipitate was extracted with methylene chloride (5x). The combined extracts were washed with brine, dried over magnesium sulfate and filtered through a silica plug. Solvents were removed under vacuum to afford 162 mg (0.92 mmol, 11%) of the product. 1H NMR (300MHz, CDCl3): 2.21 (m,2H), 2.32 (t,7Hz,2H), 2.7 (t,7Hz,2H), 6.93 (m,3H), 7.8 (br s,1H). FAB-MS: calculated for C10H10FNO 179; found 180 (M+H,100%).

Workup

  1. filtrationthen filtered
  2. additionThe chloroform layer containing hydrazoic acid
  3. customprepared by the method of Allinger and Jones, J
  4. stirringwith stirring
  5. temperaturewhile maintaining the temperature below 40° C
  6. stirringThe mixture was stirred at 40° C. for two hours
  7. waitat room temperature for 16 hours
  8. customThe mixture was transferred to a separatory funnel
  9. customthe layers were separated
  10. additionThe aqueous layer was added to ice
  11. extractionthe resulting recipitate was extracted with methylene chloride (5x)
  12. washThe combined extracts were washed with brine
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered through a silica plug
  15. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-7fb093c973b14a2f85e16d8a9352a423
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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