Hydrazine → HCID 86080526, compound

HRID 658516Notes

Reaction equation

HRID 658516 reaction equation
[NH2:1][NH2:2].Cl[C:4]([O:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[CH3:9])=[O:5]>C(Cl)Cl>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH:8]([CH3:9])[CH2:7][O:6][C:4]([NH:1][NH:2][C:4]([O:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[CH3:9])=[O:5])=[O:5])([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 114479052-(2-Nitrophenyl)propyl chloroformate

Product 1

HCID 86080526HCID 86080526, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of hydrazine (0.32 mL, 10.25 mmol) in DCM (20 mL) was added dropwise to a solution of 2-(2-nitrophenyl)propyl chloroformate (5.0 g, 20 mmol) in methylene chloride (25 mL) over a period of 30 min. The reaction mixture was stirred at room temperature for an additional 15 min. The solvent was evaporated and the residue was purified on a silica gel column. Elution of the column with 20% ethyl acetate in hexanes gave 1.46 g (3.26 mmol, 32% yield) of di-(2-(2-nitrophenyl)propoxycarbonyl)hydrazine. 1H-NMR (300 MHz, DMSO-d6): δ 9.06-8.73 (d, 1H, CONH), 7.84 (d, J=7.8 Hz, 1H, Ar—H), 7.63 (m, 2H, Ar—H), 7.48 (m, 1H, Ar—H), 4.20 (m, 2H, CH2), 3.39 (m, 1H, CH), 1.26 (d, J=6.9 Hz, 3H, CH3). 13C-NMR (75 MHz, DMSO-d6): δ 156.19 (OCOR), 149.85 (C ipso to NO2), 136.53 (C ipso to CH(CH3)CH2OCOR), 132.91 (C para to NO2), 128.52 (C para to CH(CH3)CH2OCOR), 127.76 (C ortho to CH(CH3)CH2OCOR), 123.77 (C ortho to NO2), 67.86 (CH2OCOR), 33.30 (CH), 17.99 (CH3). Mass analysis (MALDI-TOF): calculated for C20H22N4O8 446.42, found 446.24 (C20H22N4O8Na 469.38 is the major peak). TLC: 5% methanol in chloroform, Rf=0.7.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a silica gel column
  3. washElution of the column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9a24cfc751f2490ba5eea029d151aed1
Source dataset
uspto-grants-2011_12
Patent number
US08076501B2

Reaction notes

Loading…