Hydrochloric Acid → 6-Chloro-4-Hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester
Reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[CH3:16][N:17]1[C:22]2[CH:23]=[CH:24][C:25](C)=[CH:26][C:21]=2[C:20](=O)[O:19]C1=O.[ClH:30]>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:17]([CH3:16])[C:22]2[C:21]([C:20]=1[OH:19])=[CH:26][C:25]([Cl:30])=[CH:24][CH:23]=2)=[O:4])[CH3:7]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Neat diethyl malonate (2.28 g, 14.26 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 628 mg, 15.69 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred at room temperature until the evolution of hydrogen gas ceased, then the mixture was heated to 90° C. for 30 min. then cooled to room temperature. A solution of Compound 61 (12 g, 56 mmol) in dimethylacetamide was added slowly and the mixture heated overnight at 120° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 3.96 g (97%) of white solids. 1H NMR (DMSO-d6): δ 1.29 (t, J=6.9 Hz, 3H), 3.52 (s, 3H), 4.30 (q, J=6.9 Hz, 2H), 7.54 (d, J=9.1 Hz, 1H), 7.74 (dd, J=1.6, 8.9 Hz, 1H), 8.0 (m, 1H), 12.80 (b, 1H); EIMS: 282 (M+H).
Workup
- temperaturethen cooled to room temperature
- temperaturethe mixture heated overnight at 120° C
- temperatureThe mixture was cooled to room temperature
- customThe solids formed
- filtrationwere filtered
- washwashed several times by water
Sources & evidence
- ORD record
- ord-02fcda21d5084177bc68c04ccba9137c
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312220B2
Reaction notes
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