Hydrochloric Acid → Ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate

HRID 1444663Notes

Reaction equation

[CH:1](=[N:8][N:9]([C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20](OC)=[O:21])[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].O.Cl>C(O)C>[OH:21][C:20]1[C:19]2[C:18](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]([N:8]=[CH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10](=[O:17])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 2-[2-benzylidene-1-(3-ethoxy-3-oxopropanoyl)hydrazino]benzoate (5.17 g, 14.59 mmol) in ethanol (100 mL) was reacted with sodium ethoxide (21% by weight in ethanol, 5.50 mL, 14.60 mmol) at 25° C. then heated at 50° C. for 1 hour. After cooling to 25° C., the reaction mixture was poured into water, acidified to pH 4 with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent removed under vacuum to give ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate (4.51 g, 96%). MS (DCI) m/z 323 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.73 (s, 3H) 7.21 (m, 1H) 7.56 (m, 5H) 7.95 (m, 2H) 8.03 (d, J=7.72 Hz, 1H) 9.08 (s, 1H).

Workup

temperatureAfter cooling to 25° C.
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
customthe solvent removed under vacuum

Sources & evidence

ORD record: ord-dc26f50dde334585a820427ea70d880a
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662958B2

Reaction notes

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