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16th April 2019 @ 13:04

2-chloro-6-(2-hydrazinyl)(4-nitrobenzlidene)pyrazine was synthesised as one of the intermediates used for the synthesis of the final drug analogues

Risk assesment file attached below

MChem miniproject risk assessment pro-forma Nitro-benzaldehyde.pdf

Reaction scheme

    

  2-chloro-6-hydrazinopydrazine  4-Nitrobenzaldehyde Product
Mass / mg  52.0 55.0   67.3
Moles / mol  0.361 0.364  0.243 
Equivalents 1.00  1.01   /

Yield: 70%

Procedure

2-chloro-6-hydrazinopydrazine (52.0 mg, 0.361 mmol) was added to 4-Nitrobenzaldehyde (55.0mg, 0.364 mmol) and dissolved in ethanol (15 cm3) in a 50 mL round bottomed flask. The solution was put under reflux and monitored using TLC (using a solvent system of 7:3 PET ether:EtOAc) until completion. A solid crashed out throughout the reaction and the solution was found to have no remaining starting material. The solid was filtered and washed with ice cold ethanol (3 x 2 mL). . Each intermediate was characterised via 1H NMR, 13C NMR, IR, ESI MS and melting point. 

Analytical data

I3 C ASSIGNED (1).pdf
13C NMR

Intermediate 3 (4-nitro) DMSO - ASSIGNED.pdf
1H NMR

I3.pdf
IR

Intermediate3 mass spec.pdf
MS

1H NMR (300 MHz, DMSO): 8.66 (1 H, s, N=CH), 8.26 (2 H, d, J = 8.88 Hz, Ph), 8.15 (2 H, d, J = 6.09 Hz, Ph), 8.01 (2 H, d, J = 8.88 Hz, Ph), 3.33 (24 H, s, H2O).

13C NMR (75 MHz, chloroform-d): No resolved peaks.

13C NMR (75 MHz, DMSO): 147.74 (Ph-NO2), 146.03 (N=C), 140.51 (Ph-NH), 133.83 (Ph), 129.63 (Ph), 127.88 (Ph), 124.47 (Ph).

MS (TOF MS ESI+): m/z 278.0439 ([M + H]+).

Write up data 

Experiment undertaken as seen in procedure. This reaction was completed in 60 minutes

InChI Key:

2-chloro-6-hydrazinopydrazine: FEDQSVIJHNBUHH-UHFFFAOYSA-N

4-nitrobenzaldehyde: BXRFQSNOROATLV-UHFFFAOYSA-N

2-chloro-6-(2-hydrazinyl)(4-nitrobenzlidene)pyrazine: IEHJAFIAPRDGAK-LHHJGKSTSA-N

 

 

Linked Entries
Attached Files
MChem miniproject risk assessment pro-forma Nitro-benzaldehyde.pdf
i3 scheme.png
Intermediate 3 (4-nitro) DMSO - ASSIGNED.pdf
I3 C ASSIGNED (1).pdf
I3.pdf
Intermediate3 mass spec.pdf