2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → (R)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amide

HRID 1440523Notes

Reaction equation

HRID 1440523 reaction equation
[Br:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=O.[NH2:14][C:15]1[C:24]([S:25][CH3:26])=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C1(C)C=CC=CC=1>[CH3:26][S:25][C:24]1[C:15]([NH:14][C:3](=[O:5])[C@H:2]([Br:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 103976605-Amino-6-methylthioquinolineHCID 54003828(R)-2-bromodecanoic acid

Product 1

HCID 53825922(R)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amideYield 34.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(R)-2-Bromodecanoic acid (210 mg, 0.83 mmol), 5-amino-6-methylthioquinoline (160 mg, 0.84 mmol) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ, 223 mg, 0.90 mmol) were stirred in 6 ml of toluene at 0° C. The reaction was allowed to warm to rt and stirred under N2 for 18 hours. The reaction was quenched with 100 ml of 10% citric acid and extracted with ethyl acetate (3×50 ml). The organic phase was washed with 0.5N NaHCO3, brined and dried over Na2SO4. Purification by silica gel column chromatography (eluent: 100% CHCl3) yielded 120 mg (34% yield) of the desired product: 1H NMR (CDCl3) δ8.85 (1H, d, J=3 Hz), 8.09 (1H, d, J=9 Hz), 8.08 (1H, d, J=9 Hz), 7.98 (1H, bs), 7.65 (1H, d, J=9 Hz), 7.42 (1H, dd, J=9, 9 Hz), 4.61 (1H, dd, J=8, 8 Hz), 2.58 (3H, s), 2.33 (1H, m), 2.21 (1H, m), 1.76-121 (12H, m), 0.88 (3H, m).

Workup

  1. customThe reaction was quenched with 100 ml of 10% citric acid
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe organic phase was washed with 0.5N NaHCO3
  4. dry with materialdried over Na2SO4
  5. customPurification by silica gel column chromatography (eluent: 100% CHCl3)

Sources & evidence

ORD record
ord-88f64a30f2014ab2a28ec46f52c26be1
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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