Hydrochloric Acid → 2-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

HRID 2423316

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[C:9]([N+:18]([O-:20])=[O:19])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][C:28]=1[OH:29].Cl>CS(C)=O.CCOC(C)=O.O>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][C:28]=1[O:29][C:8]1[C:9]([N+:18]([O-:20])=[O:19])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2

Participants

Conditions

Temperature: 80 °C

Procedure

Cs2CO3 (15.5 g, 47.5 mmol) was added to (24.1) (3 g, 14.4 mmol) and 3-methoxy-4-hydroxyphenylacetic acid (2.63 g, 14.4 mmol) in DMSO (30 mL) at room temperature. The mixture was then stirred at 80° C. for 4 h. After cooling, the reaction mixture was treated with water (50 mL), 3N HCl (35 mL) and EtOAc (100 mL). The product was insoluble in EtOAc, but stayed in the organic layer. So the organic layer was washed with water 4 times to get rid of all the salts, and the organic layer was separated, concentrated and dried under vacuum to afford 24.2. MS ESI (pos.) m/z: 355.1 (M+H). 1H NMR (DMSO-d6) δ 8.99 (dd, 1H); 8.24 (m, 2H); 7.77 (dd, 1H); 7.29 (d, 1H); 7.21 (d, 1H); 7.18 (d, 1H); 6.96 (dd, 1H); 3.73 (s, 3H); 3.65 (s, 2H).

Workup

temperatureAfter cooling
washSo the organic layer was washed with water 4 times
customto get rid of all the salts
customthe organic layer was separated
concentrationconcentrated
customdried under vacuum

Sources & evidence

ORD record: ord-16d0c3b2ffd34074ae81e23fc3d08fa6
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960567B2

Linked notes

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