Water → HCID 89647872, compound

HRID 1399800Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH2:16][CH2:15][C:14]=1[CH2:20][NH2:21].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:21][CH2:20][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=2[Cl:12])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (3.86 g, 20 mmol), (2,3-dichlorocyclohexa-1,3-dienyl)methanamine (3.52 g, 20 mmol) and K2CO3 (4.14 g, 30 mmol) in DMF (100 mL) was stirred at 80° C. for 3 h. It was cooled to room temperature and poured into water (500 mL). It was extracted with EtOAc (300 mL×2). The combined organic layers were washed with brine (300 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with EtOAc/Pet Ether=1/6 to afford the desired product as a yellow solid (3.37 g, 51%); LC/MS: MS (ES+) m/e 332 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 4.82 (d, J=5.7 Hz, 2H), 6.84 (dd, J=0.9, 6.6 Hz, 1H), 7.28-7.34 (m, 2H), 7.55 (dd, J=2.1, 6.6 Hz, 1H), 8.48 (dd, J=0.9, 6.6 Hz, 1H), 9.22 (t, J=5.7 Hz, 1H).

Workup

temperatureIt was cooled to room temperature
extractionIt was extracted with EtOAc (300 mL×2)
washThe combined organic layers were washed with brine (300 mL×3)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel
washeluted with EtOAc/Pet Ether=1/6

Sources & evidence

ORD record: ord-03a3e61ba70f472db1536a0513710381
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906910B2

Reaction notes

Loading…