4-Fluoro-3-nitrobenzoic acid → 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide

HRID 710019Notes

Reaction equation

HRID 710019 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N([OH:23])N=NC=2C=1.CCN=C=[N:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].Cl.CCN([CH:42]([CH3:44])C)C(C)C>C(Cl)Cl.O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:28][CH2:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:44][CH2:42][C:34]2=[O:23])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 712246724-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-3-nitro-benzoic acid (5.0 g, 27.02 mmol) in CH2Cl2 (150 mL), HOBt (6.5 g, 48.63 mmol) and EDC.HCl (6.2 g, 40.53 mmol) were added followed by DIPEA (6.12 mL, 35.12 mmol). The reaction was stirred at room temperature for 6 h. Water (50.0 mL) was added and the layers were separated. Organic layer was washed with brind and concentrated to give crude product 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide (7.5 g, 90%). This was taken to the next step without further purification.

Workup

  1. customthe layers were separated
  2. washOrganic layer was washed
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-619b0411ec544e5e9628b1b41a81e9b5
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

Loading…