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

HRID 1975672Notes

Reaction equation

HRID 1975672 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 mi) 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 mi) 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 i-n vacuo, and purified by flash chromatography through silica gel 60 (300 mi) 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°-1090° C.

Workup

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

Sources & evidence

ORD record
ord-7a84b5f701914b8aa7aae9b94b81e37d
Source dataset
uspto-grants-1994_02
Patent number
US05288719

Reaction notes

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