Sodium Chloride → HCID 118276890, compound

HRID 1053697Notes

Reaction equation

HRID 1053697 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-:25])=[O:24])=[C:6]([CH:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:9](C(OC)=O)[C:10]([O:12][CH3:13])=[O:11])[CH:7]=1.[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N+:42]([O-:44])=[O:43])=[C:31]([CH:33]([CH2:38][C:39]([OH:41])=[O:40])[CH2:34][C:35]([OH:37])=[O:36])[CH:32]=1.[Cl-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-:25])=[O:24])=[C:6]([CH:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:7]=1.[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N+:42]([O-:44])=[O:43])=[C:31]([CH:33]([CH2:38][C:39]([OH:41])=[O:40])[CH2:34][C:35]([OH:37])=[O:36])[CH:32]=1

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 118276985HCID 118276985, compoundHCID 118277006HCID 118277006, compound

Product 2

HCID 118276890HCID 118276890, compoundHCID 118276985HCID 118276985, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Variant B: Adapting literature known protocols (Krapcho, Synthesis, 1982, 805-822 & 893-914; and Stowe, et al., Org. Lett., 2010, 12(4), 756-759), a solution of trimethyl 2-(5-chloro-2-nitro-phenyl)propane-1,1,3-tricarboxylate (18b′) (3.74 g, 10.0 mol) and sodium chloride (NaCl) (292 mg, 5.0 mmol) in a mixture of dimethylsulfoxide (DMSO) (23 mL) and water (780 μL) is heated to reflux for about 12 h. The reaction is monitored by TLC and/or analytical LC/MS to completion. Aqueous work-up and purification by silica gel column chromatography using ethyl acetate (EtOAc) and hexanes mixtures afford dimethyl 3-(5-chloro-2-nitro-phenyl)pentanedioate (18b″). Adapting literature known protocols (Nejman, et al., Tetrahedron, 2005, 61, 8536-854), 3-(5-chloro-2-nitro-phenyl)pentanedioic acid (18b) is prepared heating a solution of dimethyl 3-(5-chloro-2-nitro-phenyl)pentanedioate (18b″) (3.16 g, 10.0 mmol) in a mixture of 6.0 M hydrochloric acid (HCl) and 1,4-dioxane for about 12 h to reflux (105° C. oil bath temperature) to effect complete ester hydrolysis and decarboxylation. The reaction is monitored by TLC and/or analytical LC/MS to completion. The solvents are distilled off under reduced pressure using a rotary evaporator. Aqueous work-up and purification by crystallization from ethyl acetate (EtOAc) and hexanes mixtures afford the title compound (18b).

Workup

  1. customprotocols (Krapcho, Synthesis, 1982, 805-822 & 893-914; and Stowe, et al., Org. Lett., 2010, 12(4), 756-759)
  2. temperatureis heated
  3. temperatureto reflux for about 12 h
  4. customAqueous work-up and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-34eb329598c94bd5a1e4725fc9f7f255
Source dataset
uspto-grants-2016_07
Patent number
US09394236B2

Reaction notes

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