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

HRID 597199Notes

Reaction equation

HRID 597199 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]([CH3:20])[C:7](=[CH:21]O)[C:6]2=[O:23].C([O-])(=O)C.[NH4+:28]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]([CH3:20])[C:7](=[CH:21][NH2:28])[C:6]2=[O:23]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 70638946Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 53673004l-Ethyl 6,7-dimethoxy-3-aminomethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The less polar diasteriomer from the reaction of racemic ethyl 6,7-dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate with d-1-(1-naphthyl)ethylamine (see Example 18) was treated with ammonium acetate, according to the procedure of Example 19. This afforded a 46% yield of the title compound, m.p. 92°-95° C., [α]D25 = -91.52° (0.2% in CHCl3).

Sources & evidence

ORD record
ord-396ae1dd621e46e78428ade72588a36f
Source dataset
uspto-grants-1977_03
Patent number
US04013662

Reaction notes

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