7-Oxo-7-phenylheptanoic acid → 5-(6-Bromo-2-phenylquinolin-3-yl)pentanoic acid

HRID 927022Notes

Reaction equation

HRID 927022 reaction equation
O=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[NH2:17][C:18]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:19]=1[CH:20]=O>CO.[OH-].[Na+]>[Br:26][C:23]1[CH:22]=[C:19]2[C:18](=[CH:25][CH:24]=1)[N:17]=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:20]2

Participants

5

Reactant 2

HCID 3448307-Oxo-7-phenylheptanoic acidHCID 235104752-Amino-5-bromobenzaldehyde

Product 1

HCID 679816815-(6-Bromo-2-phenylquinolin-3-yl)pentanoic acidYield 102.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

7-Oxo-7-phenylheptanoic acid (5.00 g, 22.7 mmol) and 2-amino-5-bromobenzaldehyde (5.45 g, 27.2 mmol) were dissolved in a solution of methanol (100 mL) and 2 M NaOH (30 mL). The reaction mixture was heated to 110° C. in an oil bath and refluxed overnight. The reaction was concentrated, acidified with 10% aq. HCl to pH 1 and diluted with DCM. The biphasic solution was separated and the aqueous layer was extracted with DCM (3×). The combined organic phase was dried over anhydrous sodium sulfate and concentrated to provide 5-(6-bromo-2-phenylquinolin-3-yl)pentanoic acid (1A, 8.97 g, LCMS (M+H)=384).

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction was concentrated
  3. additiondiluted with DCM
  4. customThe biphasic solution was separated
  5. extractionthe aqueous layer was extracted with DCM (3×)
  6. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ec2a5b263cd40528fe0c3578c33cc8b
Source dataset
uspto-grants-2016_03
Patent number
US09290453B2

Reaction notes

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