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

HRID 1900569Notes

Reaction equation

HRID 1900569 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C:7]3[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=3[CH2:9][N:10]([C:11]([NH:13][NH2:14])=[O:12])[C:4]=2[CH:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][C:29](O)=[O:30])[CH:22]=1>C(O)(=O)C>[ClH:1].[O:30]=[C:29]([NH:14][NH:13][C:11]([N:10]1[CH2:9][C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[O:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][C:4]1=2)=[O:12])[CH2:28][CH2:27][C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 2596243-(Pyridin-3-yl)propanoic acidHCID 135604618-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide

Product 1

HCID 452615518-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(3-pyridinyl)propyl]hydrazide, monohydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The experiment described above in Example 7 was repeated on a five mmol scale with 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide (1), prepared as described above in Example 1, and 3-(3-pyridyl)propionic acid. The yield of the reaction product was 0.75 g (34%). The free base was dissolved in 5 mL of acetic acid (HOAc) and filtered. To the filtrate was added 5 mL of 6N HCl/dioxane. The hydrochloride salt was precipitated from the reaction by the addition of Et2O. The resultant solid product was collected by filtration and dried in an Abderhalden drying pistol. Analysis calculated for C22H20N4O3Cl2 : C, 57.53; H, 4.39; N, 12.20; Cl, 15.44. Found: C, 57.35; H, 4.45; N, 12.08; Cl, 15.58.

Workup

  1. customprepared
  2. filtrationfiltered
  3. additionTo the filtrate was added 5 mL of 6N HCl/dioxane
  4. customThe hydrochloride salt was precipitated from the reaction by the addition of Et2O
  5. filtrationThe resultant solid product was collected by filtration
  6. customdried in an Abderhalden
  7. customdrying pistol

Sources & evidence

ORD record
ord-dbf9c0300ed84686bb457f6c842eff89
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Reaction notes

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