Hydrochloric Acid → HCID 178479761, compound

HRID 518619Notes

Reaction equation

HRID 518619 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17]C)=[O:16])[CH2:11][CH2:10]2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][N:3]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178501197HCID 178501197, compound

Product 1

HCID 178479761HCID 178479761, compoundYield 200%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of cis-methyl 4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylate (2.51 g, 8.00 mmol) in dioxane (10 mL) was added 4N aqueous HCl (52.0 mL, 208 mmol), and the resulting mixture was stirred at 60° C. for 3 hours. The mixture was concentrated to dryness to afford cis-4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylic acid hydrochloride as a yellow solid (2.69 g, 100% yield). MS m/z=300.2 [M+H]. Calc'd for C12H14ClN3O4: 299.1.

Workup

  1. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-8938de081afd4e619f1e5419f50c3329
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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