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

HRID 2425522노트

반응식

HRID 2425522 반응식
[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

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimide2회HCID 6737103-Methyl-2-phenylquinoline-4-carboxylic acid

생성물 1

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

시약·촉매·용매 4

HCID 7187Benzoyl Peroxide촉매2회HCID 962Water용매HCID 5943Carbon Tetrachloride용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ce067a246cd54402bf11d0c9fe8beb54
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964733B2

반응 노트

불러오는 중…