Hydrochloric Acid → HCID 15168508, compound

HRID 484419Notes

Reaction equation

HRID 484419 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18](=[O:20])[CH3:19])[C:5](=C=O)[C@H:6](OC)[NH:7]2.[OH-:21].[Li+].Cl.[CH3:24][OH:25]>O>[C:24]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18](=[O:20])[CH3:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:25])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium Hydroxide2×HCID 86747044HCID 86747044, compound

Product 1

HCID 15168508HCID 15168508, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of trans-5,7-dichloro-2-methoxy-carbonyl-4-acetylamino-1,2,3,4-tetrahydroquinoline (0.12 g, 0.379 mmol) in methanol (5 ml) was added aqueous lithium hydroxide (0.42 ml of a 1.0M solution, 0.42 mmol) and the resulting mixture was stirred at room temperaure for 7 hours. To this mixture was added additional aqueous lithium hydroxide (0.20 ml of a 1.0M solution, 0.20 mmol) and the mixture was stirred for a further 16 hours. The solution was evaporated to dryness in vacuo and the residue obtained was redissolved in water (50 ml). The solution was acidified to pH 1 with dilute hydrochloric acid and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (30 ml), dried (Na2SO4) and evaporated to give the pure title compound as colourless crystals (0.108 g, 223-225 pc); δ (360 MHz, methanol) 1.70 (1H, ddd, J=13.3, 12.8 and 4.0 Hz, CHACHBHCCHD), 1.95 (3H, s, COCH3), 2.41 (1H, dm, J=13.3 Hz, CHACHBHCCHD), 3.92 (1H, dd, J=12.8 and 3.0 Hz, CHACHBHCCHD), 5.17 (1H, m, CHACHBHCCHD), 6.66 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.72 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e 302 (M+), 198 (100%, m-NHCOCH3, CO2H, H); found: C, 47.65; H, 4.11; N, 9.07. C12H12Cl2N2O3 requires C, 47.55; H, 3.99; N, 9.24%.

Workup

  1. stirringwas stirred for a further 16 hours
  2. customThe solution was evaporated to dryness in vacuo
  3. customthe residue obtained
  4. extractionextracted with ethyl acetate (2×30 ml)
  5. washThe combined extracts were washed with brine (30 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-79fa52efcc424b35b0b1c2a3f706fb08
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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