Hydrochloric Acid → Tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate

HRID 1892489Notes

Reaction equation

HRID 1892489 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[C:25]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:28])[NH:26][NH2:27].Cl>O1CCCC1.C(OCC)(=O)C>[NH:26]([C:25]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:27][C:13]([O:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74944-Nitrophenethyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazate

Product 1

HCID 58112038Tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(4-nitrophenyl)ethanol (5.015 g, 30.00 mmol) in anhydrous tetrahydrofuran (50 ml) was added 1,1′-carbonyldiimidazole (5.839 g, 36.01 mmol), and the mixture was stirred at room temperature for 30 min. tert-Butyl carbazate (5.956 g, 45.06 mmol) was added, and the mixture was stirred at room temperature for 16 hr and further at 50° C. for 8 hr. 0.5M Hydrochloric acid (100 ml) and ethyl acetate (100 ml) were added to the reaction mixture, and the mixture was stirred, stood still and then partitioned. The organic layer was washed with 0.5M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:hexane=4:6→5:5) to give tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate (9.780 g, quantitative) as a slightly yellow solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. washThe organic layer was washed with 0.5M hydrochloric acid, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:hexane=4:6→5:5)

Sources & evidence

ORD record
ord-2386e79899354cd189c443a9b10038e4
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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