HCID 15168441, compound → HCID 15168442, compound

HRID 484413Notes

Reaction equation

HRID 484413 reaction equation
C([N:4]1[C:13]2[C:8](=[C:9]([Cl:15])[CH:10]=[C:11]([Cl:14])[CH:12]=2)[C:7](=[O:16])[CH2:6][CH:5]1[C:17]([OH:19])=[O:18])(=O)C>Cl>[C:17]([CH:5]1[CH2:6][C:7](=[O:16])[C:8]2[C:13](=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[NH:4]1)([OH:19])=[O:18]

Participants

3

Reactant 1

HCID 15168441HCID 15168441, compound

Product 1

HCID 15168442HCID 15168442, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-Acetyl-2-carboxy-5,7-dichloro-4-oxo-1,2,3,4-tetrahydroquinoline (21.17 g) was suspended in 3N hydrochloric acid (500 ml) and heated at reflux overnight. After cooling, the aqueous solution was extracted with ethyl acetate (3×300 ml) and the combined organic layers were washed with brine (1×300 ml), dried (MgSO4), filtered and evaporated in vacuo to give the title compound as a yellow solid (17.45 g, m.p. 218°-219° C.); δ (360 MHz, DMSO) 2.73 (1H, dd, J=15.7 and 6.8 Hz, CHACHBHC), 2.92 (1H, dd, J=15.7 and 6.2 Hz, CHACHBHC), 4.36 (1H, m, CHACHBHC), 6.67 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.96 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.62 (1H, br, s, NH); m/e (FAB) 260 (M+1); Found: C, 46.10; H, 2.85; N, 5.26. C10H7Cl2NO3 requires C, 46.18; H, 2.71; H, 5.39%.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. extractionthe aqueous solution was extracted with ethyl acetate (3×300 ml)
  5. washthe combined organic layers were washed with brine (1×300 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-bb824656600d4e2da273a381dde85840
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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