Oxalic Acid → 2-Cyclopropylethyl-hydrazine oxalate salt

HRID 30983Notes

Reaction equation

HRID 30983 reaction equation
C(OC([NH:6][NH:7][CH2:8][CH2:9][CH:10]1[CH2:12][CH2:11]1)=O)C.[OH-].[Na+].[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17]>>[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17].[CH:10]1([CH2:9][CH2:8][NH:7][NH2:6])[CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 45123072N'-(2-Cyclopropylethyl)hydrazinecarboxylic acid ethyl ester

Product 1

HCID 693101202-Cyclopropylethyl-hydrazine oxalate saltYield 70.9%

Conditions

Temperature
120 °C

Procedure

N′-(2-Cyclopropylethyl)hydrazinecarboxylic acid ethyl ester (5a) (2.2 g, 12.6 mmol) was suspended in 7 mL of a 40% aqueous NaOH solution. The biphasic mixture was heated for 12 h at 120° C., upon which it was cooled to room temperature and partitioned between brine and CH2Cl2. The organic layer was removed, dried over MgSO4, and filtered. Oxalic acid (1.1 g, 12.6 mmol) was added to the filtrate, which after 12 h was filtered and dried in vacuo to yield 1.7 g (50%) of the oxalate salt (6a) as a white powder. 1H-NMR (400 MHz, D2O): 3.13 (t, 2H, J=7.2 Hz); 1.46 (q, 2H, J=7.2 Hz); 0.61 (m, 1H); 0.1 (d, 2H); 0.39 (m, 2H); 0.01 (m, 2H) ppm.

Workup

  1. temperaturewas cooled to room temperature
  2. custompartitioned between brine and CH2Cl2
  3. customThe organic layer was removed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. filtrationwas filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-05d8cfd1237c44fda7fd808f4ebabbd7
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

Loading…