Ammonia → N-(Cyclopropylmethyl)-3-hydrazinylbenzamide

HRID 1596514Notes

Reaction equation

HRID 1596514 reaction equation
C(OC([NH:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:22])[NH:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH:11]=1)=O)(C)(C)C.Cl.C(OCC)(=O)C.N>C(OCC)(=O)C>[CH:19]1([CH2:18][NH:17][C:16]([C:12]2[CH:11]=[C:10]([NH:9][NH2:8])[CH:15]=[CH:14][CH:13]=2)=[O:22])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21701855HCID 21701855, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 21701848N-(Cyclopropylmethyl)-3-hydrazinylbenzamideYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 5 ml of ethyl acetate, 1.92 g of 1-tert-butoxycarbonyl-2-[3-(N-cyclopropylmethylcarbamoyl)phenyl]hydrazine was dissolved and about 12 ml of 2N hydrochloric acid/ethyl acetate solution was added to the solution. The resulting suspension was stirred at room temperature for 4 hours. To the reaction mixture, 15 ml of aqueous 2N ammonia solution was added and the resultant was extracted with 20 ml of ethyl acetate. The extract was dried and concentrated to obtain 1.28 g of crude crystals. The crude crystals were recrystallized from ethyl acetate-hexane to obtain 1.20 g (yield 93%) of the captioned compound.

Workup

  1. extractionthe resultant was extracted with 20 ml of ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated
  4. customto obtain 1.28 g of crude crystals
  5. customThe crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cc0eed208dba4846b1760784042c27d8
Source dataset
uspto-grants-2001_09
Patent number
US06291470B1

Reaction notes

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