Ethylene Glycol → 4-chloro-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoic acid

HRID 425966Notes

Reaction equation

[OH-:1].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10]C(C#N)=[C:6]([NH:12][C@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]2[N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:5]=1.Cl.[CH2:25]([OH:28])[CH2:26]O>>[Cl:3][C:4]1[CH:11]=[CH:10][C:26]([C:25]([OH:28])=[O:1])=[C:6]([NH:12][C@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]2[N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:5]=1

Participants

Reactant 4

HCID 174Ethylene Glycol

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 667036344-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzonitrile

Product 1

HCID 667037374-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoic acid

Conditions

Temperature: 190 °C

Procedure

Ethylene glycol and sodium hydroxide were added to 4-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzonitrile, followed by stirring at 190° C. for 5 hours. After neutralizing the reaction liquid by adding hydrochloric acid, the organic layer was extracted with chloroform and the solvent was evaporated to obtain 4-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoic acid.

Workup

customthe reaction liquid
extractionthe organic layer was extracted with chloroform
customthe solvent was evaporated

Sources & evidence

ORD record: ord-2e0c103a276e4f428f3a16ede5fcdb5b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106190B2

Reaction notes

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