Ammonium Acetate → l-Ethyl 6,7-dimethoxy-3-aminomethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

HRID 328805Notes

Reaction equation

O[CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]1[CH3:23].C([O-])(=O)C.[NH4+:28]>C(O)C>[NH2:28][CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]1[CH3:23]

Participants

Conditions

Temperature: 40 °C

Procedure

A reaction mixture comprising 58.5 g. of 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester and 58.5 g. of ammonium acetate in 730 ml. of ethanol is heated to reflux for 10 min. The mixture is cooled to 40° C. and concentrated to a yellow solid. Th residue is taken up in 800 ml. of chloroform which is subsequently washed successively with water (1 × 450 ml.), 1N aqueous sodium hydroxide (2 × 450 ml.) and a brine solution (1 × 450 ml.). The chloroform layer is separated, dried over magnesium sulfate and concentrated to a yellow solid, 87.0 g., m.p. 86°-150° C. The crude product is further purified by recrystallization from ethyl acetate-hexane, 43.3 g., m.p. 160°-161° C.

Workup

temperatureto reflux for 10 min
concentrationconcentrated to a yellow solid
washof chloroform which is subsequently washed successively with water (1 × 450 ml.), 1N aqueous sodium hydroxide (2 × 450 ml.)
customThe chloroform layer is separated
dry with materialdried over magnesium sulfate
concentrationconcentrated to a yellow solid, 87.0 g
customThe crude product is further purified by recrystallization from ethyl acetate-hexane, 43.3 g

Sources & evidence

ORD record: ord-2dc1496a676d4ad6920cc384f65426de
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04018758

Reaction notes

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