Water → HCID 86639114, compound

HRID 2359841Notes

Reaction equation

[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Mg]Br.O>C1COCC1>[Cl:1][C:2]1[C:11]([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH3:16])[OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Chloro-6-methoxyquinoline-3-carbaldehyde (2.66 g, 12 mmol) was dissolved in THF (40 mL) under nitrogen and cooled to −78° C. At this temperature, a solution of 2-methoxyphenyl magnesium bromide (1M, 12.1 mL, 13.32 mmol) in THF was added by drops. Then the mixture was heated slowly to room temperature. The batch was mixed with water and extracted several times with ethyl acetate. The combined organic phases were washed with water until neutral, dried (sodium sulfate) and concentrated. Yield: 3.9 g (11.8 mmol, 99%).

Workup

temperatureThen the mixture was heated slowly to room temperature
extractionextracted several times with ethyl acetate
washThe combined organic phases were washed with water until neutral,
dry with materialdried (sodium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-808ec6fc1470445d8a379e49f2906527
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686002B2

Reaction notes

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