8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]hydrazide → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-(3-amino-1-oxopropyl)hydrazide, monohydrochloride

HRID 275290Notes

Reaction equation

HRID 275290 reaction equation
CC(C)(OC([NH:7][CH2:8][CH2:9][C:10]([NH:12][NH:13][C:14]([N:16]1[CH2:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[O:19][C:18]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:17]1=2)=[O:15])=[O:11])=O)C.Cl.O1CCOCC1>C(O)(=O)C>[ClH:31].[NH2:7][CH2:8][CH2:9][C:10]([NH:12][NH:13][C:14]([N:16]1[CH2:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[O:19][C:18]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:17]1=2)=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 152373958-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]hydrazideHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 1317177198-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-(3-amino-1-oxopropyl)hydrazide, monohydrochlorideYield 163.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2.30 g (5.0 mmol) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]hydrazide (7), prepared as described above in Example 7, in 8 mL of acetic acid (HOAc) was added 8 mL of 6.8N HCl/dioxane. After 15 minutes, the solvent was removed under H2O aspirator vacuum. The resulting residue was triturated with diethyl ether (Et2O). The resulting white solid was collected on a sintered glass funnel and dried in a vacuum oven at 70° C. for 16 hours. A yield of 1.62 g (81%) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-(3-amino-1-oxopropyl)hydrazide, monohydrochloride (9) was isolated.

Workup

  1. customthe solvent was removed under H2O
  2. customThe resulting residue was triturated with diethyl ether (Et2O)
  3. customThe resulting white solid was collected on a sintered glass funnel
  4. customdried in a vacuum oven at 70° C. for 16 hours

Sources & evidence

ORD record
ord-3709a7b17bf643dab92eb8d3ff3bd5f3
Source dataset
uspto-grants-1995_02
Patent number
US05393747

Reaction notes

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