Diethyl Ether → cis-2-Carboxy-4-oxo-3,5,7-trimethyl-1,2,3,4-tetrahydroquinoline

HRID 484414Notes

Reaction equation

HRID 484414 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].CC[O:12][C:13]([CH:15]([C:17]([C:19]([O:21]CC)=[O:20])=O)[CH3:16])=O.C(OCC)C>O>[C:19]([C@H:17]1[C@@H:15]([CH3:16])[C:13](=[O:12])[C:6]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:8][C:7]=2[CH3:9])[NH:5]1)([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 79493,5-DimethylanilineHCID 97750Butanedioic acid, 2-methyl-3-oxo-, 1,4-diethyl ester

Product 1

HCID 15168457cis-2-Carboxy-4-oxo-3,5,7-trimethyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

These compounds were prepared by the route outlined in Example 1 using 3,5-dimethyl aniline and diethyloxalpropionate as the starting materials in the first step. The cis and the trans isomers were distinguished by X-ray crystallography. Trans isomer (Example 3) [m.p. 156°-157° C. (diethyl ether)]; δ (360 MHz, CDCl3), 1.35 (3H, d, J=7.2 Hz, CH3CHBCHA), 2.23 (3H, s, CH3Ar), 2.54 (3H, s, CH3Ar), 2.97 (1H, m, CH3CHBCHA), 3.97 (1H, d, J=4.9 Hz, CH3CHACHB), 6.40 (2H, s, 6-H and 8-H); m/e 233 (M+), 188 (100%, -CO2H); Found: C, 66.73; H, 6.50; N, 5.95. C13H15NO3 requires C, 66.94; H, 6.48; N. 6.00%. Cis-isomer (Example 4) (oil); δ (250 MHz, CDCl3) 1.17 (3H, d, J=7.2 Hz, CH3CHBCHA). 2.24 (3H, s, CH3Ar), 2.57 (3H, s, CH3Ar), 2.95 (1H, dq, J=7.2 and 4.0 Hz, CH3CHBCHA), 4.43 (1H, d, J=4.0 Hz, CH3CHBCHA), 4.90 (1H, br, s, NH), 6.40 (1H, s, 6-H or 8-H), 6.42 (1H, s, 6-H or 8-H); m/e 233 (M+), 188 (100%, M-CO2H); Found: C, 64.97; H, 6.53; N, 5.72. C13H15NO3.0.4 H2O requires C, 64.93; H, 6.62; N, 5.82%.

Workup

  1. customThese compounds were prepared by the route

Sources & evidence

ORD record
ord-2c6506b9b54d464a92e2794ead8cd67e
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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