Hydrochloric Acid → 3-(Bromomethyl)-2-phenylquinoline-4-carboxylic acid

HRID 2425522Notes

Reaction equation

HRID 2425522 reaction equation
[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:21]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl.O.C(OCC)(=O)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:21][CH2:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimide2×HCID 6737103-Methyl-2-phenylquinoline-4-carboxylic acid

Product 1

HCID 234976523-(Bromomethyl)-2-phenylquinoline-4-carboxylic acidYield 108.8%

Reagents, catalysts & solvents 4

HCID 7187Benzoyl PeroxideCatalyst2×HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methyl-2-phenylquinoline-4-carboxylic acid (1.5 g, 5.7 mmol) and N-bromosuccinimide (1.52 g, 8.5 mmol) in carbon tetrachloride (25 mL) was added benzoyl peroxide (approximately 10 mg) and heated under reflux with illumination using a long wavelength ultraviolet lamp (Blak-ray model B100-AP, Upland, Calif.). After 4 h, additional portions of N-bromosuccinimide (750 mg, 4.2 mmol) and benzoyl peroxide (approximately 10 mg) were added. After an additional 2 h, the cooled mixture was diluted with water. Sodium thiosulfate (1 g) was added, then the pH was adjusted to approximately 4.0 by addition of dilute HCl and NaOH. The mixture was further diluted with ethyl acetate, extracted, and dried (MgSO4) to afford the product as a light brown powder (1.62 g, 6.2 mmol). 1H NMR (300 MHz, DMSO) δ 8.09 (d, J=8.4 Hz, 1H), 7.96-7.86 (m, 2H), 7.76 (d, J=8.2 Hz, 1H), 7.68-7.64 (m, 2H), 7.61-7.55 (m, 3H), 4.75 (s, 2H). LRMS m/z 342.0.

Workup

  1. temperatureheated
  2. temperatureunder reflux with illumination
  3. waitAfter an additional 2 h
  4. extractionextracted
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ce067a246cd54402bf11d0c9fe8beb54
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

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