Sodium Hydroxide → Sodium 5''-chloro-2,2':5',3''-terpyridine-3'-carboxylate

HRID 1802359Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([O:22]C)=[O:21])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:12][CH:13]=2)[CH:5]=[N:6][CH:7]=1.[OH-].[Na+:25]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([O-:22])=[O:21])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:12][CH:13]=2)[CH:5]=[N:6][CH:7]=1.[Na+:25]

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of methyl 5″-chloro-2,2′:5′,3″-terpyridine-3′-carboxylate (12-3, 3.05 g, 9.36 mmol, 1.0 equiv) in THF/methanol (22 mL/4.5 mL) was added 10 N sodium hydroxide (1.124 mL, 11.2 mmol, 1.2 equiv) and the system was heated to 135° C. for 15 minutes in a microwave reactor. The reaction mixture was cooled, concentrated, and azeotroped with ethyl acetate (2×100 mL) and toluene (3×100 mL) to afford the desired product (12-4) as a white solid. ESI+MS [M+H]+ C16H10ClN3O2 calc'd 312.0. found 311.9.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
customazeotroped with ethyl acetate (2×100 mL) and toluene (3×100 mL)

Sources & evidence

ORD record: ord-5cbc15212d9c427fa89aff58e372b658
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349872B2

Reaction notes

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