Hydrazine hydrate (1:1) → 3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-t-butyl acetate

HRID 2351227Notes

Reaction equation

HRID 2351227 reaction equation
[O:1]=[C:2]1[CH:8]([N:9]2C(=O)C3=CC=CC=C3C2=O)[CH2:7][CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[N:3]1[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O.NN>C(O)C>[NH2:9][CH:8]1[CH2:7][CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[N:3]([CH2:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14010679tert-butyl 2-oxo-3-phthalimido-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate

Product 1

HCID 36741653-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-t-butyl acetateYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml of ethanol is added 10 g of tert-butyl 2-oxo-3-phthalimido-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate, and 5 g of hydrazine hydrate is added to the mixture, followed by refluxing for 2 hours. The reaction mixture is concentrated under reduced pressure, and 300 ml of water is added to the residue, followed by extraction with 200 ml of ethyl acetate. The extract is washed with 1N aqueous sodium hydroxide and water, successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crystals, which separate out, are treated with a mixture of ether and petroleum ether and collected by filtration to give 6 g of tert-butyl 3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate as colorless prisms. m.p. 121°-122° C.

Workup

  1. additionis added to the mixture
  2. temperatureby refluxing for 2 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure, and 300 ml of water
  4. additionis added to the residue
  5. extractionfollowed by extraction with 200 ml of ethyl acetate
  6. washThe extract is washed with 1N aqueous sodium hydroxide and water
  7. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crystals, which separate out
  10. additionare treated with a mixture of ether and petroleum ether
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3eba275d2fbb4dcc9c3cbc24de956f9c
Source dataset
uspto-grants-1989_10
Patent number
US04871842

Reaction notes

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