Sulfuric Acid → 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 2059299Notes

Reaction equation

HRID 2059299 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH2:13][C:14]2=[O:17])=[CH:9][CH:8]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:17])[NH:1][C:15]=2[CH:16]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4 g of sodium azide are added portionwise to 8.3 g of 7-methoxy-1-tetralone in 36 ml of acetic acid. Then 17 ml of concentrated sulphuric acid are added dropwise, without a rise in temperature over 40°; the solution is poured onto ice and neutralised with 2 N sodium hydroxide solution. The separating bulk of crystals is removed and recrystallised from ethyl acetate. One obtains 6.4 g of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (m.p. 137°-138°).

Workup

  1. customThe separating bulk of crystals is removed
  2. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-4c47795adde74da0954b17145309aafe
Source dataset
uspto-grants-1982_03
Patent number
US04322439

Reaction notes

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