Sodium Hydroxide → HCID 15168488, compound

HRID 484463Notes

Reaction equation

HRID 484463 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:14][C@H:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:21])=[CH:10][C:11]=2[Cl:20])[NH:6]1)=[O:4].[OH-].[Na+]>CC(C)=O>[C:3]([C@H:5]1[CH2:14][C@H:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:21])=[CH:10][C:11]=2[Cl:20])[NH:6]1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67856775HCID 67856775, compound

Product 1

HCID 15168488HCID 15168488, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Trans-2-methoxycarbonyl-4-methoxycarbonylmethyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (0.4 g, 0.0012 mol) was dissolved in 50% aqueous acetone and cooled to 0° C. whereupon 0.5N sodium hydroxide solution (2.42 ml, 1 molar equivalent) was added. The reaction mixture was allowed to warm slowly to room temperature and stirred for 14 h. The acetone was removed under vacuum and the aqueous residue acidified to pH 1 with 1N hydrochloric acid and extracted into ethyl acetate (2×50 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to leave a residue which was purified by chromatography on silica gel using 4% methanol/1% acetic acid in dichloromethane as eluent to give the title compound (0.26 g, m.p. 181°-182° C.) as a colourless solid; δ (250 MHz, CDCl3) 1.72 (1H, ddd, J=13.3, 12.5 and 4.0 Hz, CHACHBHCCHD), 2.36 (1H, dm, J=13.3 Hz, CHACHBHCCHD), 2.39 (1H, dd, J=16.0 and 11.2 Hz, CHEHFCO2CH3), 2.72 (1H, dd, J=16.0 and 3.5 Hz, CHEHFCO2CH3), 3.66 (1H, m, CHACHBHCCHDCH2CH3), 3.73 (3H, s, CO2CH3), 3.99 (1H, dd, J=12.5 and 5.1 Hz, CHACHBHCCHDCH2CO2Me), 515 (1H, br, s, NH), 6.56 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.62 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e 317 (M+); Found C, 49.17; H, 4.13; N, 4.42. C13H13Cl2NO4 requires C, 49.08; H, 4.12; N, 4.40%.

Workup

  1. additionwas added
  2. customThe acetone was removed under vacuum
  3. extractionextracted into ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto leave a residue which
  8. customwas purified by chromatography on silica gel using 4% methanol/1% acetic acid in dichloromethane as eluent

Sources & evidence

ORD record
ord-c37b56abf351437a8b05305dcf5f6e5a
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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