Potassium Carbonate → HCID 178479762, compound

HRID 518776Notes

Reaction equation

HRID 518776 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.O1CCOCC1>O>[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 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 122757652,4-Dichloro-5-nitropyridineHCID 178511567HCID 178511567, compound

Product 1

HCID 178479762HCID 178479762, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 (20.00 mL). 2,4-Dichloro-5-nitropyridine (6.75 g, 35.0 mmol) was added to the reaction mixture as a dioxane (40 mL) solution. The reaction mixture was stirred at 80° C. for 8 hours. The reaction mixture was concentrated under vacuum to remove the dioxane and the remaining aqueous solution was acidified with aqueous 2N HCl (approximately pH 2-3). A precipitate formed which was collected on a glass frit washing well with water and then with DCM. The solid was dried under high vacuum at 37° C. 8.79 g of trans-4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylic acid hydrochloride (74.8% yield) was collected as a yellow solid. Mass cal'd: 299.1; MS (ESI pos. ion) m/z: 300.0 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto remove the dioxane
  3. customA precipitate formed which
  4. customwas collected on a glass frit
  5. washwashing well with water
  6. customThe solid was dried under high vacuum at 37° C

Sources & evidence

ORD record
ord-f6d55c6171f0457085fe2cab71904930
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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