Hydrochloric Acid → 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one

HRID 2381069Notes

Reaction equation

Cl.C1(C[O:6][C:7]2[C:8]([O:27][CH3:28])=[CH:9][CH:10]=[C:11]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]=[C:12]3[NH:18][C:19]2[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=2[Cl:26])CC1>CO>[Cl:26][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Cl:25])[C:19]=1[NH:18][C:12]1[C:11]2[C:16](=[C:7]([OH:6])[C:8]([O:27][CH3:28])=[CH:9][CH:10]=2)[NH:15][C:14](=[O:17])[CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Concentrated HCl (15 ml) was added to a solution of 8-(cyclopropylmethoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (1.2 g, 2.90 mmol, Example 3) and methanol (8 ml). The reaction mixture was heated at 50° C. for 4 h and then concentrated. The residue was neutralized with sat'd NaHCO3, filtered (washed with ethanol and ether), and dried to give 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one: MS (ESI): 352.

Workup

concentrationconcentrated
filtrationfiltered
wash(washed with ethanol and ether)
customdried

Sources & evidence

ORD record: ord-55ac309c165d4e6f869618096355acaa
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258154B2

Reaction notes

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