8-chlorodibenz[b,f][1,4]oxazepine-10(11H)carboxylic acid, 2-[1-oxo-3-(2-pyridinyl)propyl]hydrazide → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(2-pyridinyl)propyl]hydrazide, monohydrochloride

HRID 1900567

Reaction equation

HRID 1900567 reaction equation
[O:1]=[C:2]([NH:11][NH:12][C:13]([N:15]1[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][C:17]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:16]1=2)=[O:14])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1>C(O)C>[ClH:30].[O:1]=[C:2]([NH:11][NH:12][C:13]([N:15]1[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][C:17]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:16]1=2)=[O:14])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 1

HCID 149759858-chlorodibenz[b,f][1,4]oxazepine-10(11H)carboxylic acid, 2-[1-oxo-3-(2-pyridinyl)propyl]hydrazide

Product 1

HCID 452615528-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(2-pyridinyl)propyl]hydrazide, monohydrochlorideYield 153.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.64 g of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)carboxylic acid, 2-[1-oxo-3-(2-pyridinyl)propyl]hydrazide (6), prepared as described above in Example 6, was taken up in 25 mL of 3A ethanol and filtered to remove any undissolved material. The solution was cooled in an ice bath with stirring. To this was added dropwise 5.3 mL of 9.5M hydrogen chloride in ethanol. After stirring in the ice bath for 5 minutes, some of the product precipitated. This was poured slowly into 275 mL of stirring diethyl ether (Et2O), and the resulting mixture was stirred for 5 minutes. The resulting solid product was collected by filtration, washed with 20 mL of 3 A ethanol, followed by Et2O, and dried under vacuum at 56° C. to yield 2.20 g (76.7%) of a white powder. Analysis calculated for C22H20N4O3Cl2 : C, 57.53; H, 4.39; N, 12,20; Cl, 15.44; Found: C, 57.31; H, 4.36; N, 11.98; Cl, 15.11.

Workup

  1. filtrationfiltered
  2. customto remove any undissolved material
  3. temperatureThe solution was cooled in an ice bath
  4. additionTo this was added dropwise 5.3 mL of 9.5M hydrogen chloride in ethanol
  5. stirringAfter stirring in the ice bath for 5 minutes
  6. customsome of the product precipitated
  7. additionThis was poured slowly into 275 mL of stirring diethyl ether (Et2O)
  8. stirringthe resulting mixture was stirred for 5 minutes
  9. filtrationThe resulting solid product was collected by filtration
  10. washwashed with 20 mL of 3 A ethanol
  11. customdried under vacuum at 56° C.

Sources & evidence

ORD record
ord-81ec6b5a90e94aa1928f3730dd71351f
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Linked notes

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