Pyridine → 326901-33-1

HRID 881577Notes

Reaction equation

HRID 881577 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].N1C=CC=CC=1>ClCCCl.C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:8])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6877Ethyl 2-aminobenzoateHCID 110872-Nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 710775326901-33-1

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A catalytic amount of DMF was added to a stirred solution of 2-nitrobenzoic acid (2.30 g, 13.8 mmol) and oxalyl chloride (6.0 mL, 69 mmol) in 1,2-dichloroethane (70 mL) at r.t. and under nitrogen flow. After 1 h, the reaction was concentrated, re-dissolved in 1,2-dichloroethane and concentrated again. The crude was immediately dissolved in 1,2-dichloroethane (25 mL) before ethyl 2-aminobenzoate (1.00 mL, 6.76 mmol) and pyridine (1.70 mL, 21.0 mmol) was added. The reaction was stirred 45 min at r.t. and under nitrogen atmosphere before being diluted with DCM and washed with HCl (aq., 1M), NaHCO3 (aq., sat., 2×) and brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The crude was purified by column chromatography (SiO2, toluene:acetone 100:0→98:2) to give compound 20 in quant yield (2.24 g).

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionre-dissolved in 1,2-dichloroethane
  3. concentrationconcentrated again
  4. additionwas added
  5. washwashed with HCl (aq., 1M), NaHCO3 (aq., sat., 2×) and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified by column chromatography (SiO2, toluene:acetone 100:0→98:2)

Sources & evidence

ORD record
ord-ebf66eca340e4cd2b48bab055247977c
Source dataset
uspto-grants-2015_03
Patent number
US08993622B2

Reaction notes

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