Hydrazine hydrate (1:1) → N-(2,5-diamino-4-chlorobenzyl)pivalamide

HRID 508872Notes

Reaction equation

HRID 508872 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([Cl:16])[C:13]([N+:17]([O-])=O)=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].O.NN>CO.[Ni]>[NH2:1][C:2]1[CH:15]=[C:14]([Cl:16])[C:13]([NH2:17])=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90018960N-(2-amino-4-chloro-5-nitrobenzyl)pivalamide

Product 1

HCID 90019665N-(2,5-diamino-4-chlorobenzyl)pivalamideYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-amino-4-chloro-5-nitrobenzyl)pivalamide (2.0 g, 6.9 mmol) in methanol (20 mL), Raney Ni (2.0 g) and hydrazine hydrate (5.0 mL) were added and the reaction mass was stirred at RT for 3 h. After the completion of the reaction, the reaction mass was filtered through celite pad and obtained filtrated was concentrated to afford 1.5 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.11 (s, 9H), 3.97 (br d, 2H), 4.52 (br d, 2H), 5.44 (br s, 2H), 6.50 (d, J=11.4 Hz, 2H), 7.88 (m, 1H).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mass was filtered through celite pad
  3. customobtained
  4. filtrationfiltrated
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-e10136300f1e4c16b1feac43a52424fb
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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