1,1-Dimethylethyl 2-[[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylate → tert-Butyl 2-{[4-(pyridin-2-yl)phenyl]methyl}hydrazine-1-carboxylate

HRID 843278Notes

Reaction equation

HRID 843278 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[C].[Pd].C(O)(C)C>[C:1]([O:5][C:6](=[O:7])[NH:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 533949851,1-Dimethylethyl 2-[[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 9796325tert-Butyl 2-{[4-(pyridin-2-yl)phenyl]methyl}hydrazine-1-carboxylateYield 83.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
5 °C

Procedure

N-(tert-Butoxycarbonyl)-N′-[4-(pyridin-2-yl)phenylmethylidene]hydrazine (20 g, 67.3 mmol), isopropyl alcohol (80 ml) and palladium-carbon (1 g) were charged in a 300 ml four-necked flask and hydrogen was added at 50° C. under atmospheric pressure. Hydrogen was continuously added for 8 hr under the same conditions. The reaction mixture was filtered to remove the catalyst. After 90% of isopropyl alcohol in the obtained filtrate was evaporated by concentration, the same volume of heptane was added. The mixture was cooled with stirring and crystals were precipitated at around 40° C. The mixture was further cooled to 5° C. with stirring and the precipitated crystals were collected by filtration and dried to give 16.91 g of tert-butyl3-[4-(pyridin-2-yl)benzyl]carbazate as white crystals. The yield was 84.0% of N-(tert-butoxycarbonyl)-N′-[4-5 (pyridin-2-yl )phenylmethylidene]hydrazine

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. customAfter 90% of isopropyl alcohol in the obtained filtrate was evaporated by concentration
  4. additionthe same volume of heptane was added
  5. temperatureThe mixture was cooled
  6. customcrystals were precipitated at around 40° C
  7. stirringwith stirring
  8. filtrationthe precipitated crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-f7380cb09dd346e88973c954a17b3b5e
Source dataset
uspto-grants-2002_04
Patent number
US06376678B1

Reaction notes

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