1,2-Dichloroethane → HCID 3118727, compound

HRID 510473Notes

Reaction equation

HRID 510473 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.CC[N:16]([CH:20]([CH3:22])C)[CH:17]([CH3:19])C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.N1CCCC1>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:5]([N:16]2[CH2:17][CH2:19][CH2:22][CH2:20]2)=[O:7])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 183703-Methyl-4-nitrobenzoic acidHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 3118727HCID 3118727, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-4-nitrobenzoic acid (0.5 g, 2.76 mmol) in DMF (4 mL) was added DIPEA (0.9 mL, 5.79 mmol), followed by HOBT (0.39 g, 2.89 mmol), EDC (0.44 g, 2.89 mmol) and pyrrolidine (0.196 g, 2.76 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then diluted with water and extracted with EtOAc. The organic layer was washed with brine, then concentrated to provide crude material which was further purified by column chromatography (silica:100-200 mesh, MeOH:DCM 8-10%), to afford the title compound (0.31 g, 48.1%). LCMS (ES+) 235.05 (M+H)+, RT 2.04 minutes (method 1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customto provide crude material which
  5. customwas further purified by column chromatography (silica:100-200 mesh, MeOH:DCM 8-10%)

Sources & evidence

ORD record
ord-e4fef6f591ad4f26b65ac799d1a433e2
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Reaction notes

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