Sulfuric Acid → Methyl 6-bromoquinoline-3-carboxylate

HRID 1894955Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2.S(=O)(=O)(O)O.[C:20](=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:20])=[O:13])=[CH:5]2

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 6-bromoquinoline-3-carboxylic acid (3 g, 11.9 mmol), in methanol (55 mL) was added sulfuric acid (0.32 mL, 6 mmol). The reaction was stirred at 85° C. for 96 h. The reaction was then cooled to room temperature and saturated sodium bicarbonate solution was added until pH=7. On neutralization, methyl 7-bromo-2-naphthoate precipitated as a solid which was collected by suction filtration (Int-1, 2.77 g, 97%). LC-MS: (FA) ES+ 266; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.33 (d, J=2.1 Hz, 1H), 9.01 (d, J=2.1 Hz, 1H), 8.53 (t, J=1.3, 1.3 Hz, 1H), 8.07-8.01 (m, 2H), 3.95 (s, 3H).

Workup

temperatureThe reaction was then cooled to room temperature
customOn neutralization, methyl 7-bromo-2-naphthoate precipitated as a solid which
filtrationwas collected by suction filtration (Int-1, 2.77 g, 97%)

Sources & evidence

ORD record: ord-6a4fc7b24771433da36fa2f3d02e45b8
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513421B2

Reaction notes

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