Hydrazine hydrate (1:1) → 3-Amino-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one

HRID 1632773Notes

Reaction equation

HRID 1632773 reaction equation
C1(=O)[N:5]([CH:6]2[C:12](=[O:13])[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8][CH2:7]2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH:6]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 133751583-phthalimido-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

Product 1

HCID 133751543-Amino-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.85 g of 3-phthalimido-2,3-dihydro-1,5-benzoxazepin-4(5H)-one in 60 ml of absolute ethanol is treated with 0.31 ml of hydrazine hydrate and the reaction mixture is heated to reflux for 1.5 hr. After cooling to room temperature, the solid is removed by filtration and the filtrate is concentrated in vacuo. The residue is dissolved in chloroform and filtered and concentrated a second time to afford 3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one; m.p. 65°-70°; NMR (CDCl3) δ 6.50-7.60 (m, 4), 3.60-5.30 (m, 3), 3.25 [d (broad), 1].

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 1.5 hr
  3. customthe solid is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in chloroform
  6. filtrationfiltered
  7. concentrationconcentrated a second time

Sources & evidence

ORD record
ord-5f8560ccd68c4a4e8a223956c250db74
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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