Hydrochloric Acid → 6-Fluoro-2-(4-(morpholinomethyl)phenyl)quinoline-4-carboxylic acid

HRID 516960Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=O)[CH3:27])=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.[OH-:29].[K+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:26]([C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:16]3[CH2:17][CH2:18][O:13][CH2:14][CH2:15]3)=[CH:25][CH:24]=1)[CH:27]=[C:5]2[C:6]([OH:11])=[O:29]

Participants

Conditions

Temperature: 125 °C

Procedure

In a 20 ml microwave vial, 5-fluoroisatin (650 mg, 4 mmol) was suspended in ethanol (7 ml), then, 1-[4-(morpholinomethyl)phenyl]ethanone (preparation 6) (863 mg, 4 mmol) was added followed by water (7 ml). To this suspension potassium hydroxide (2.21 g, 39 mmol) was added at room temperature. The microwave vial was sealed and the reaction mixture was heated at 125° C. for 20 min under microwave irradiation. The resulting solution was diluted with water (50 ml) and adjusted to pH 7-8 with 10% HCl. The resulting precipitate was filtered and washed with water (50 ml) and ethyl acetate (100 ml) to obtain the desired product as an off-white solid (1.1 g, Yield: 76%).

Workup

customThe microwave vial was sealed
filtrationThe resulting precipitate was filtered
washwashed with water (50 ml) and ethyl acetate (100 ml)

Sources & evidence

ORD record: ord-5e4397e8cd224994be0546dd8b05d8e5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115088B2

Reaction notes

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