Ethylamine hydrochloride → HCID 10821337, compound

HRID 2237646Notes

Reaction equation

HRID 2237646 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl.[CH2:13]([NH2:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:13]([NH:15][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH3:14]

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 10821337HCID 10821337, compoundYield 81,447.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2,4-difluoro-1-nitrobenzene (0.50 g, 0.003 mmol), ethylamine hydrochloride (0.49 g, 0.006 mmol), K2CO3 (1.66 g, 0.012 mmol) in acetonitrile (30 mL) was stirred at room temperature for 16 hours and then filtered. The filtrate was concentrated and dissolved in small amount of CHCl3. Purification by column chromatography on silica using pentane/diethyl ether 95:5 as eluent gave 0.45 g of a yellow solid. 1H NMR (CDCl3) δ 8.23-8.18 (m, 1H), 8.08 (br s, 1H), 6.49-6.45 (m, 1H), 6.38-6.32 (m, 1H), 3.34-3.27 (m, 2H), 1.38 (tr, J=7.22 Hz, 3H); 13CNMR (CDCl3) δ 167.55 (d, JCF=255.6 Hz), 147.4 (d, JCF=12.9 Hz), 129.91 (d, JCF=12.9 Hz), 128.71 (br s), 103.73 (d, JCF=24.8 Hz), 99.14 (d, JCF=27.6 Hz), 37.88, 14.05; MS (posESI) m/z=found 184.0653, calc 184.0648. Anal. (C12H18N4O2) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in small amount of CHCl3
  4. customPurification by column chromatography on silica

Sources & evidence

ORD record
ord-ba30b8b9c61a470a9a44b8d00f73366d
Source dataset
uspto-grants-2010_05
Patent number
US07718650B2

Reaction notes

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