Hydrazine hydrate (1:1) → 10-(Aminoacetyl)-8-chloro-10,11-dihydrodibenz-[b,f][1,4]oxazepine

HRID 248822Notes

Reaction equation

HRID 248822 reaction equation
O.NN.[Cl:4][C:5]1[CH:33]=[CH:32][C:8]2[O:9][C:10]3[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=3[CH2:12][N:13]([C:14](=[O:27])[CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)[C:7]=2[CH:6]=1>C(O)C>[NH2:16][CH2:15][C:14]([N:13]1[CH2:12][C:11]2[CH:28]=[CH:29][CH:30]=[CH:31][C:10]=2[O:9][C:8]2[CH:32]=[CH:33][C:5]([Cl:4])=[CH:6][C:7]1=2)=[O:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 106697298-chloro-10,11-dihydro-10-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl]dibenz[b,f][1,4]oxazepine

Product 1

HCID 1066106110-(Aminoacetyl)-8-chloro-10,11-dihydrodibenz-[b,f][1,4]oxazepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (1.25 mL) and 8-chloro-10,11-dihydro-10[(1,3-dihydro-1,3-dioxo-2H -isoindol-2-yl)acetyl]-dibenz[b,f][1,4]-oxazepine (5.00 grams) were refluxed in absolute ethanol (125 mL) for 4 hours. The resulting mixture was filtered hot, and the collected solid was rinsed twice with ethanol, and then with hot methylene chloride. The filtrate and rinses were combined, evaporated in vacuo, and purified by flash chromatography through silica gel 60 (300 mL) using 95:5:0.5 chloroform:methanol:ammonium hydroxide. Trituration of the purified product with ethyl ether/hexane yielded the title compound as a white solid. Yield: 2.91 grams (84%). Mp: 108°-109° C.

Workup

  1. filtrationThe resulting mixture was filtered hot
  2. washthe collected solid was rinsed twice with ethanol
  3. customevaporated in vacuo
  4. custompurified by flash chromatography through silica gel 60 (300 mL)

Sources & evidence

ORD record
ord-e43bda1414734a7183d57efaf204eeec
Source dataset
uspto-grants-1993_05
Patent number
US05212169

Reaction notes

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