Hydrochloric Acid → 1-amino-3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxyquinolin-2(1H)-one

HRID 601181Notes

Reaction equation

HRID 601181 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([N:12]=CC2C=CC=CC=2)[C:4](=[O:20])[C:3]=1[C:21](OCC)=O.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH2:36])(=[O:35])=[O:34].Cl>C1(C)C=CC=CC=1>[NH2:12][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:21]2[NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33](=[O:34])(=[O:35])[N:36]=2)[C:4]1=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 728942-AminobenzenesulfonamideHCID 67063863Ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 1363552751-amino-3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxyquinolin-2(1H)-oneYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

The product of Example 226C (4.51 g, 14.00 mmol) was reacted with 2-amino benzenesulfonamide (2.41 g, 14.00 mmol) in toluene (65 mL) at reflux for 6 hours. After cooling to 25° C., the solid (5.52 g) was collected by filtration and reacted further with aqueous 10% potassium hydroxide (100 mL) for 8 hours at 130° C. After cooling to 25° C., the reaction was poured into ice and acidified to pH 2 with 1 M hydrochloric acid. The resulting solid was isolated by filtration and dried to give the title compound (3.50 g, 71%). The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) δ 5.31 (s, 2 H) 7.05 (t, J=8.09 Hz, 1 H) 7.27 (m, 2 H) 7.53 (m, 2 H) 7.67 (m, 2 H) 8.07 (dd, J=8.09, 1.47 Hz, 1 H) 16.38 (s, 1 H).

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationthe solid (5.52 g) was collected by filtration
  3. customreacted further with aqueous 10% potassium hydroxide (100 mL) for 8 hours at 130° C
  4. temperatureAfter cooling to 25° C.
  5. additionthe reaction was poured into ice
  6. customThe resulting solid was isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-ad2cb260034042a2a5318db44705f2a3
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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