Potassium Carbonate → HCID 178479762, compound

HRID 518669Notes

Reaction equation

HRID 518669 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:23]=[C:22](Cl)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1>O.O1CCOCC1>[ClH:17].[Cl:17][C:18]1[CH:23]=[C:22]([NH:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]2)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122757652,4-Dichloro-5-nitropyridineHCID 178511567HCID 178511567, compound

Product 1

HCID 178479762HCID 178479762, compoundYield 149.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

trans-4-Aminocyclohexanecarboxylic acid (5.01 g, 35.0 mmol) and potassium carbonate (4.83 g, 35.0 mmol) were dissolved in water (20 mL). 2,4-Dichloro-5-nitropyridine (6.75 g, 35.0 mmol) was added as a solution in dioxane (40 mL), and the reaction was stirred at 80° C. for 8 hours. The dioxane solvent was removed under vacuum. The remaining aqueous solution was acidified with aqueous 2N HCl (approx. pH 2-3), and the resulting precipitate was collected and washed with water, and then DCM. The solid was dried under high vacuum to yield trans-4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylic acid hydrochloride as a yellow solid (8.79 g, 74.8% yield). MS m/z=300.0 [M+H], calc 299.71 for C12H14ClN3O4.

Workup

  1. customThe dioxane solvent was removed under vacuum
  2. customthe resulting precipitate was collected
  3. washwashed with water
  4. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-7f343414996541d188b9c339b08141e9
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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