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

HRID 1095789Notes

Reaction equation

C1(C[O:5][C:6]2[C:7]([O:26][CH3:27])=[CH:8][CH:9]=[C:10]3[C:15]=2[NH:14][C:13](=[O:16])[CH:12]=[C:11]3[NH:17][C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[CH:20][C:19]=2[Cl:25])CC1.Cl>O>[Cl:25][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Cl:24])[C:18]=1[NH:17][C:11]1[C:10]2[C:15](=[C:6]([OH:5])[C:7]([O:26][CH3:27])=[CH:8][CH:9]=2)[NH:14][C:13](=[O:16])[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 8-(cyclopropylmethoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (99%. 23.8 g, 57.9 mmol) and conc. HCl (150 mL) was warmed at 40° C. for 30 min and then water (0° C., 150 mL) was added. The resulting mixture was stirred vigorously at 0° C. for 1 h, filtered, and then washed with water (0° C., 100 mL). A mixture of the resulting solid and 0.5 M pH 7 phosphate buffer (300 mL) was stirred vigorously at 0° C. for 30 min, filtered, washed with water (0° C., 300 mL), and then dried in an oven to give 19.9 g of 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.69 (s, 1H), 9.51 (s, 1H), 8.78 (s, 3H), 7.65 (d, 1H), 7.01 (d, 1H), 3.90 (s, 3H); MS (ESI): 352.2.

Workup

filtrationfiltered
washwashed with water (0° C., 100 mL)
additionA mixture of the resulting solid and 0.5 M pH 7 phosphate buffer (300 mL)
stirringwas stirred vigorously at 0° C. for 30 min
filtrationfiltered
washwashed with water (0° C., 300 mL)
customdried in an oven

Sources & evidence

ORD record: ord-8884591e99474a0f863884646781971f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138205B2

Reaction notes

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