Benzenesulfonyl chloride → HCID 22556005, compound

HRID 985167Notes

Reaction equation

HRID 985167 reaction equation
[NH2:1][C:2]1[C:3](=[O:16])[N:4]([CH2:12][C:13]([OH:15])=[O:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:17]1([S:23]([NH:1][C:2]2[C:3](=[O:16])[N:4]([CH2:12][C:13]([OH:15])=[O:14])[C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 14627640HCID 14627640, compound

Product 1

HCID 22556005HCID 22556005, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[3-Amino-2-oxo-2H-quinolin-1-yl]acetic acid, (0.206 g, 0.81 mmol) was treated with benzenesulfonyl chloride (0.172 g, 0.97 mmol) in pyridine for one hour. After removing the pyridine, the residue was recrystallized in acetone to yield a white crystal solid as the product, 2-[3-benzenesulfonylamino-2-oxo-2H-quinolin-1-yl]acetic acid, (EX-4A)(0.117 g, y=41%). HPLC-MS (0 to 95% AcCN/6 min @ 1.0 mL/Min @ 254 nm @ 50° C.): retention time 2.85 min, M+H+=359.2 for formula C17H15N2O2S. 1H NMR (400 MHz, Acetone-d6): d 5.12 (s, 2H), 7.28 (t, J=7.2 Hz, 1H), 7.36 (d, J=8.8 Hz, 1H), 7.48-7.63 (m, 4H), 7.75 (dd, J=8, 1.6 Hz, 1H), 7.74 (s, 1H), 8.00-8.03 (m, 2H). 13C NMR (101 MHz, Acetone-d6): d (ppm) 44.8, 115.0, 120.8, 120.9, 123.9, 127.8, 128.1, 129.4, 129.9, 130.1, 134.2, 136.7, 140.4, 158.2, 169.1.

Workup

  1. customAfter removing the pyridine
  2. customthe residue was recrystallized in acetone

Sources & evidence

ORD record
ord-a0464bc97bfa41558bac916d2320d1d4
Source dataset
uspto-grants-2005_03
Patent number
US06870056B1

Reaction notes

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