Hydrochloric Acid → HCID 66746690, compound

HRID 2279411Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](N)[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][CH3:14].Cl.N([O-])=[O:17].[Na+].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:17])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][CH3:14]

Participants

Conditions

Temperature: 4 °C

Procedure

A mixture of 7-fluoro-6-methoxy-quinolin-3-ylamine (prepared according to procedures described in FR2862301, 830 mg, 4.3 mmol, 1.0 eq) and concentrated hydrochloric acid (12N, 3.0 g, 30.2 mmol, 7.0 eq) is stirred at 4° C. before the addition of sodium nitrite (313 mg, 4.7 mmol, 1.1 eq) in water (24 mL). After 2 hours stirring at 4° C., the resulting mixture is added dropwise to a stirred solution of concentrated sulfuric acid (8.2 mL) and water (24 mL) at 90° C. within 10 minutes. After 1 hour stirring at 90° C. the reaction mixture is cooled down to room temperature, neutralized with sodium hydrogen carbonate and extracted with ethyl acetate (3×80 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is recrystallized in methanol to afford 7-fluoro-6-methoxy-quinolin-3-ol as an off-white solid (0.60 g, 72% yield).

Workup

stirringAfter 1 hour stirring at 90° C. the reaction mixture
temperatureis cooled down to room temperature
extractionextracted with ethyl acetate (3×80 mL)
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude product that
customis recrystallized in methanol

Sources & evidence

ORD record: ord-7b8345d507734123b4875ebf9cc70a7b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133219B2

Reaction notes

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