Sodium Hydroxide → 2-(Methylamino)quinoline-6-carboxylic acid

HRID 537153Notes

Reaction equation

[OH-].[Na+].[CH3:3][NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=2)[N:6]=1>C(O)C>[CH3:3][NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=2)[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Aqueous sodium hydroxide (4 mL, 8 mmol, 2 N) was added to a solution of ethyl 2-(methylamino)quinoline-6-carboxylate (850 mg, 3.7 mmol) in ethanol (10 mL). The reaction was heated to 50° C. overnight. Ethanol was removed in vacuo and the residue was acidified to pH=5 with 1 N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (710 mg, 96%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ): 8.26 (d, 1H), 7.96-7.93 (m, 2H), 7.50 (d, 1H), 7.43 (d, 1H), 6.81 (d, 1H), 2.91 (d, 3H).

Workup

customEthanol was removed in vacuo
filtrationThe resulting precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-641edba148eb4b9ab69ea878fe9ec798
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859773B2

Reaction notes

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