Methanol → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(ethoxyhydroxyphosphinyl)acetyl]hydrazide

HRID 1974531Notes

Reaction equation

HRID 1974531 reaction equation
[CH2:1]([O:3][P:4]([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:6]CC)=[O:5])[CH3:2].CO.[OH-].[Na+]>C1COCC1>[CH2:1]([O:3][P:4]([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])([OH:6])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 99562598-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(diethoxyphosphinyl)acetyl]hydrazide

Product 1

HCID 99548798-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(ethoxyhydroxyphosphinyl)acetyl]hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 0.58 g (1.2 mmol) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(diethoxyphosphinyl)acetyl]hydrazide (20), prepared as described above in Example 20, in 5 mL of THF:methanol (THF:MeOH) (3:2) was added 2 mL of N NaOH. After 24 hours of stirring, an additional 2 mL of NaOH was added to the reaction. After 7 days of stirring, the reaction mixture was filtered, and the resulting filtrate was extracted with 25 mL of EtOAc. The aqueous layer was neutralized with N HCl to pH 2, and was extracted with 25 mL of dichloromethane (DCM). The organic layer was dried over Na2SO4 anhydrous, filtered, and then concentrated in vacuo. The yield of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(ethoxyhydroxyphosphinyl)acetyl]hydrazide (27), which was a beige foam, was 0.20 g (37%). Analysis calculated for C18H19N3O6PCl. 025 H2O (M.W. 443.30): C, 48.66; H, 4.42; N, 9.46. Found: C, 48.62; H, 4.37; N, 9.24.

Workup

  1. stirringAfter 7 days of stirring
  2. filtrationthe reaction mixture was filtered
  3. extractionthe resulting filtrate was extracted with 25 mL of EtOAc
  4. extractionwas extracted with 25 mL of dichloromethane (DCM)
  5. dry with materialThe organic layer was dried over Na2SO4 anhydrous
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87edd9741a2f4ce3ba48720eeab44b15
Source dataset
uspto-grants-1994_02
Patent number
US05283240

Reaction notes

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