1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Methyl 4-cyano-3-fluorobenzoate

HRID 219767Notes

Reaction equation

HRID 219767 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[F:12])#[N:2].Cl.[CH3:14]N(C)CCCN=C=NCC>CO.CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:14])=[O:8])=[CH:5][C:4]=1[F:12])#[N:2]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27784684-Cyano-3-fluorobenzoic acid

Product 1

HCID 17965941Methyl 4-cyano-3-fluorobenzoateYield 87.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

4-Cyano-3-fluorobenzoic acid (Carbocore, 1 g; 6.06 mmol) was dissolved in MeOH (12.50 mL) to which 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.39 g; 7.27 mmol) followed by 4-dimethylaminopyridine (0.07 g; 0.61 mmol) were added. The mixture was stirred at RT overnight after which it was concentrated, taken up in EtOAc and washed with 0.1N HCl, 0.1 N NaOH and brine (2×50 mL each) and dried over MgSO4 to give the title compound as an off-white solid (0.95 g; 87%). 1H NMR: (DMSO-d6, 300 MHz) δ 8.16 (dd, J=6.40 Hz, J=7.91 Hz, 1H), 8.02 (dd, J=1.50 Hz, J=9.80 Hz, 1H), 7.97 (dd. J=1.50 Hz, J=7.91, 1H), 3.95 (s, 3H). GC/MS (M+·): 179 (EI). HPLC (Method A) Rt 3.17 min (Purity: 87.3%).

Workup

  1. additionwere added
  2. concentrationwas concentrated
  3. washwashed with 0.1N HCl, 0.1 N NaOH and brine (2×50 mL each)
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-22512fadcb434e08988f54501bb7caec
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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