Ethylenediamine → 2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

HRID 558036Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH2:9]([NH2:12])[CH2:10][NH2:11].BrN1C(=O)CCC1=O.[OH-].[Na+]>C(Cl)Cl>[NH:11]1[CH2:10][CH2:9][N:12]=[C:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Pyridinecarboxaldehyde (0.95 ml, 10 mmol) is added into a reaction flask containing 20 ml of methylene chloride and ethylene diamine (0.78 ml, 10.5 mmol) is added. After the reaction is carried out at 0° C. for 20 minutes, N-bromosuccinimide (1.87 g, 10.5 mmol) is added. The reaction temperature is slowly raised from 0° C. to the room temperature and the reaction is further carried out for 24 hrs at the room temperature. 10% sodium hydroxide solution is added to have the solution become alkaline. After extraction with a small amount of methylene chloride is carried out for 2 times, the organic layer is collected and concentrated to obtain white solids. After purified by silicone chromatographic column, the product pyil is obtained. The yield is about 90%. 1H NMR (400 MHz, CDCl3): δ 8.55-8.54 (m, 1 H), 8.11 (d, 1 H, J=7.6 Hz), 7.76-7.71 (m, 1 H), 7.34-7.21 (m, 1 H), 3.82 (s, 4 H).

Workup

additionis added
waitthe reaction is further carried out for 24 hrs at the room temperature
extractionAfter extraction with a small amount of methylene chloride
customthe organic layer is collected
concentrationconcentrated
customto obtain white solids
customAfter purified by silicone chromatographic column
customthe product pyil is obtained

Sources & evidence

ORD record: ord-84b64c3dcc6a4540a7112aa5e6998345
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08062767B2

Reaction notes

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