Hydrochloric Acid → 1-amino-3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxyquinolin-2(1H)-one

HRID 601279

Reaction equation

[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][C:17]=2[S:30]([NH2:33])(=[O:32])=[O:31])=O)[C:3]1=[O:34].Cl>[OH-].[K+]>[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:18][C:17]=3[S:30](=[O:32])(=[O:31])[N:33]=2)[C:3]1=[O:34]

Participants

Conditions

Temperature: 125 °C

Procedure

The product of Example 304E (3.13 g, 6.51 mmol) was suspended in 10% potassium hydroxide solution (50 mL), heated at 125° C. for 24 hours then at 140° C. for 24 hours. The mixture was poured into ice and 1 M hydrochloric acid, filtered, and dried to give the title compound (2.03 g, 67%). MS (ESI−) m/z 461 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.18 (s, 2 H) 5.33 (s, 2 H) 7.06 (m, 1 H) 7.25 (m, 3 H) 7.43 (m, 6 H) 7.69 (d, J=7.72 Hz, 1 H) 8.06 (d, J=8.09 Hz, 1 H) 16.31 (s, 1 H).

Workup

filtrationfiltered
customdried

Sources & evidence

ORD record: ord-c6ed92d1900f40c8a9659ddc30e54cb1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Linked notes

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