Hydrochloric Acid → 6-((3-Fluorophenyl)amino)-4-(propylamino)nicotinic acid

HRID 2284811Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:19]=[C:18]([NH:20][CH2:21][CH2:22][CH3:23])[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl>C(O)C.O1CCCC1.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:19]=[C:18]([NH:20][CH2:21][CH2:22][CH3:23])[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 6-((3-fluorophenyl)amino)-4-(propylamino)nicotinate (S15, 247 mg) in ethanol (3 mL) and tetrahydrofuran (1.5 mL), 2.0 mol/L aqueous sodium hydroxide (0.78 mL) was added at room temperature, and the mixture was stirred at 50° C. for 1 hour. To the reaction mixture, 2.0 mol/L aqueous sodium hydroxide (0.39 mL) was added at 50° C., and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was cooled to room temperature, and then 1.0 mol/L aqueous hydrochloric acid was added to the reaction mixture until the mixture became acidic. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 6-((3-fluorophenyl)amino)-4-(propylamino)nicotinic acid (S16, 130 mg).

Workup

stirringthe mixture was stirred at the same temperature for 3 hours
temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid matter was taken by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-76c54f410f2448199640d20835ccf9cd
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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