Sodium Hydroxide → HCID 15168492, compound

HRID 484464Notes

Reaction equation

HRID 484464 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:14][C@H:13]([CH2:15][C:16]([O:18]C)=[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+]>CO>[C:3]([C@H:5]1[CH2:14][C@H:13]([CH2:15][C:16]([OH:18])=[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 15168492HCID 15168492, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Trans-2-methoxycarbonyl-4-methoxycarbonylmethyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (Example 156a) (0.4 g, 0.0012 mol) was dissolved in 50% aqueous methanol (80 ml) with sodium hydroxide (1 g). The reaction mixture was heated at 70° C. for 14 h and the solvents removed under vacuum. The residue was dissolved in water (50 ml), acidified to pH 1 with 1 normal hydrochloric acid and extracted into ethyl acetate (2×50 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was purified by recrystallisation from diethyl ether/hexane to give the title compound as a colourless solid (0.24 g, m.p. 229°-231° C.); δ (250 MHz, DMSO) 1.63 (1H, ddd, J=13.3, 12.4 and 4.0 Hz, CHACHBHCCHD), 2.20 (1H, dm, J=13.3 Hz, CHACHBHCCHD), 2.40 (2H, m, CHEHFCO2H), 3.39 (1H, m, CHACHBHCCHDCHEHFCO2H), 3.98 (1H, dd, J=12.4 and 3.3 Hz, CHACHBHCCHD), 6.57 (1H, br, s, NH), 6.61 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.80 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e (FAB) 304 (M+1); Found C, 47.56; H, 3.70; N, 4.57 C12H11Cl2NO4 requires C, 47.39; H, 3.65; N, 4.61%.

Workup

  1. customthe solvents removed under vacuum
  2. dissolutionThe residue was dissolved in water (50 ml)
  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 give a residue which
  8. customwas purified by recrystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-63324a6826fe46d28a0e5f2e0c92547a
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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