Sodium Hydroxide → HCID 67856686, compound

HRID 484425Notes

Reaction equation

HRID 484425 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:20][C@@H:19]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C:18]2[C:13](=[CH:14][C:15](Cl)=[CH:16][C:17]=2Cl)[NH:12]1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>CO.O>[CH2:24]([O:23][C:21]([C@H:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C@@H:11]([C:9]([OH:10])=[O:8])[CH2:20]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67856715HCID 67856715, compound

Product 1

HCID 67856686HCID 67856686, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Cis-2,4-dibenzyloxycarbonyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (0.23 g) was dissolved in 50% aqueous methanol (30 ml) and 1N sodium hydroxide (0.54 ml, 1.1 molar equivalents) was added and the reaction mixture was stirred for 14 h at room temperature. The solvents were removed in vacuo to give a residue which was dissolved in water (30 ml) and washed with diethyl ether (2×30 ml). The aqueous layer was acidified to pH 1 with dilute hydrochloric acid and extracted into diethyl ether (2×30 ml) then dried (Na2SO4), filtered and concentrated in vacuo to leave a residue which was purified by chromatography on silica gel with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane as eluent. The solid obtained on evaporation was recrystallised from diethyl ether/hexane to give, as a colourless solid, cis-4-benzyloxycarbonyl-2-carboxy-1,2,3,4-tetrahydroquinoline (0.027 g, m.p. 144° C. dec). δ (360 MHz, CDCl3) 2.35 (1H, m, CHACHBHCCHD), 2.81 (1H, dm, J=13.9 Hz, CHACHBHCCHD), 4.03 (2H, m, CHACHBHCCHD), 5.07 (2H, s, PhCH2), 6.57 (1H, d, J=1.5 Hz, 6-H or 8-H), 6.77 (1H, d, J=1.5 Hz, 6-H or 8-H), 7.32 (5H, m, Ph); m/e 379 (M+), 198 (100%); Found: C, 56.53; H, 4.00; N, 3.65 . C18H15Cl2NO4 requires C, 56.86; H, 3.98; N, 3.68%.

Workup

  1. customThe solvents were removed in vacuo
  2. customto give a residue which
  3. washwashed with diethyl ether (2×30 ml)
  4. extractionextracted into diethyl ether (2×30 ml)
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto leave a residue which
  9. customwas purified by chromatography on silica gel with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane as eluent
  10. customThe solid obtained on evaporation
  11. customwas recrystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-7022dd3e97024035bc5b6450a136d1c4
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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