Hydrazine hydrate (1:1) → HCID 20449954, compound

HRID 358067Notes

Reaction equation

HRID 358067 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][N:16]4C(=O)C5=CC=CC=C5C4=O)=[N:13][N:14]=[C:10]3[CH2:9][CH:8]=[C:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:6]=2[CH:34]=1.O.NN>C(O)C>[NH2:16][CH2:15][C:12]1[N:11]2[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:34][C:6]=3[C:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])=[CH:8][CH2:9][C:10]2=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20450017HCID 20450017, compound

Product 1

HCID 20449954HCID 20449954, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

235 mg of 8-chloro-1-(phthalimidomethyl)-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine are dissolved in 15 ml of ethanol and treated with 500 ml of hydrazine hydrate. The mixture is stirred at room temperature for 2 hours and then the ethanol is evaporated in vacuo. The residue is dissolved in ethyl acetate, washed twice with water, dried and evaporated. The residue is chromatographed on 10 g of aluminium oxide (neutral, activity grade III). By elution with chloroform/ethanol (9:1) and crystallization from ethyl acetate there is obtained 1-(aminomethyl)-8-chloro-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine of melting point 187°-190°.

Workup

  1. customthe ethanol is evaporated in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed twice with water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on 10 g of aluminium oxide (neutral, activity grade III)
  7. washBy elution
  8. customwith chloroform/ethanol (9:1) and crystallization from ethyl acetate

Sources & evidence

ORD record
ord-5220ab90c543474f8e03ca92f3d4232f
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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