1-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol → 1-((4-(4-Amino-2-fluorophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol

HRID 2277371Notes

Reaction equation

[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.C(O[K])=O>C1COCC1.O.[Pd]>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[CH:12][CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:24]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 1-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol (10.04 g, 27 mmol) and HCOOK (15.87 g, 189 mmol) in THF/H2O (54 mL, THF/H2O=4:1) was added catalytic amount of Pd/C (5%, 53%˜55% water content, w/w). The reaction was stirred at 45° C. for 5 hours, and then diluted with THF/H2O (40 mL, v/v=1:1). The resulted mixture was filtered and the filtrate was concentrated in vacuo. The residue was washed with EtOH/H2O (30 mL×3, v/v=5:1), and dried in vacuo at 45° C. for 24 hours to give the title compound as a light gray solid (8.1 g, 87%).

Workup

filtrationThe resulted mixture was filtered
concentrationthe filtrate was concentrated in vacuo
washThe residue was washed with EtOH/H2O (30 mL×3, v/v=5:1)
customdried in vacuo at 45° C. for 24 hours

Sources & evidence

ORD record: ord-11c363c1d4aa4f64bb0d59af923941f1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

Loading…