Acetic Acid → HCID 21956403, compound

HRID 2213832Notes

Reaction equation

[C:1](#[N:3])[CH3:2].C([Li])CCC.CN(/[CH:12]=[N:13]/[C:14]1[C:23]([C:24]([O:26]C)=O)=[CH:22][C:21]2[C:16](=[CH:17][C:18]([O:30][CH3:31])=[C:19]([O:28][CH3:29])[CH:20]=2)[N:15]=1)C.C(O)(=O)C>O1CCCC1>[CH3:29][O:28][C:19]1[C:18]([O:30][CH3:31])=[CH:17][C:16]2=[N:15][C:14]3[NH:13][CH:12]=[C:2]([C:1]#[N:3])[C:24](=[O:26])[C:23]=3[CH:22]=[C:21]2[CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Acetonitrile (1.3 mL, 24.9 mmol) is added to a −78° C. solution of 9.0 mL of 2.5 M n-butyllithium (22.5 mmol) in 40 mL of tetrahydrofuran. After stirring at −78° C. for 15 min, a solution of 2.86 g (9.02 mmol) of methyl 2-{[(E)-(dimethylamino)methylidene]amino}-6,7-dimethoxy-3-quinolinecarboxylate in 100 mL of tetrahydrofuran is added dropwise over 30 minutes. After stirring at −78° C. for 30 minutes, the reaction mixture is allowed to warm to room temperature and then stirred at room temperature for 1 hour. The reaction mixture is cooled to −78° C. and 3.0 mL of acetic acid is added. The mixture is then stirred at room temperature for 40 min. The solids are collected by filtration washing with water, methanol and ethyl acetate to provide 1.11 g (44%) of 7,8-dimethoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carbonitrile as a light yellow solid, mp>300° C. MS 281.9 (M+H)+ Analysis for C15H11N3O3.0.65H2O Calcd: C, 61.49; H, 4.23; N, 14.34. Found: C, 61.40; H, 4.40; N, 14.70.

Workup

stirringAfter stirring at −78° C. for 30 minutes
temperatureto warm to room temperature
stirringstirred at room temperature for 1 hour
temperatureThe reaction mixture is cooled to −78° C.
stirringThe mixture is then stirred at room temperature for 40 min
filtrationThe solids are collected by filtration
washwashing with water, methanol and ethyl acetate

Sources & evidence

ORD record: ord-dec16a7721504c96b5771b224bbe245d
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105531B2

Reaction notes

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