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

HRID 2425522ノート

反応式

HRID 2425522 の反応式
[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

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 7187Benzoyl Peroxide触媒2 回HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ce067a246cd54402bf11d0c9fe8beb54
出典データセット
uspto-grants-2011_06
特許番号
US07964733B2

反応ノート

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