Hydrochloric Acid → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carboxylic acid

HRID 2246781Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:13].[Na+].P([O-])([O-])(O)=[O:16].[Na+].[Na+].[ClH:22]>C(O)C>[Cl:22][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([OH:16])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a room temperature solution of 1-(6-chloropyridin-3-yl)cyclopropanecarbonitrile from Step 3 (5.3 g) in ethyl alcohol (60 mL) was added a solution of 30 mL of sodium hydroxide (25% NaOH w/w in water). The mixture was heated at 100° C. for 8 hours. It was cooled to room temperature and poured into saturated aqueous disodium hydrogen phosphate (at 0° C.) and an adjusted pH at 4 with hydrogen chloride (1 N). The mixture was extracted with dichloromethane (2×100 mL) and the combined extracts were washed with brine, dried with magnesium sulfate and the solvent was removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound.

Workup

temperatureIt was cooled to room temperature
extractionThe mixture was extracted with dichloromethane (2×100 mL)
washthe combined extracts were washed with brine
dry with materialdried with magnesium sulfate
customthe solvent was removed in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-c929beb9d5ec454fabac4672b0b5ccb5
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687524B2

Reaction notes

Loading…