Succinic anhydride → HCID 67691185, compound

HRID 484441Notes

Reaction equation

HRID 484441 reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:15][C@H:14]([NH2:16])[C:13]2[C:8](=[CH:9][C:10]([Cl:18])=[CH:11][C:12]=2[Cl:17])[NH:7]1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>C(OCC)(=O)C>[CH3:2][O:3][C:4]([C@H:6]1[CH2:15][C@H:14]([NH:16][C:25]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:31])[C:13]2[C:8](=[CH:9][C:10]([Cl:18])=[CH:11][C:12]=2[Cl:17])[NH:7]1)=[O:5]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 11430Potassium CarbonateHCID 67690826HCID 67690826, compound

Product 1

HCID 67691185HCID 67691185, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of trans-2-methoxycarbonyl-5,7-dichloro-4-amino-1,2,3,4-tetrahydroquinoline hydrochloride (Example 9a) (225 mg, 0.819 mmol) in ethyl acetate (50 ml) was added a solution of potassium carbonate (50 ml). The mixture was shaken until no solid remained (5 min). The organic layer was retained and washed with brine (50 ml) before drying (Na2SO4). The solvent was removed in vacuo. The residue was redissolved in xylene (20 ml) and succinic anhydride (90 mg, 0.901 mmol) was added. The mixture was heated, with stirring, in an oil bath (80° C.) for 16h. The precipitate was removed by filtration and washed with ether to give the title compound as a colourless crystalline solid. δ (DMSO, 250 MHz), 1.65 (1H, ddd, J=13.0, 12.7 and 3.7 Hz, CHACHBHCCHD), 2.15 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 2.18-2.41 (4H, m, CO(CH2)2CO), 3.73 (3H, s, CH3), 3.94 (1H, dd, J 13.0 and 3.0 Hz, CHACHBHCCHd), 5.01 (1H, m, CHACHBHCCHD), 6.69 (1H, J=2.1 Hz, 6-H or 8-H), 6.86 (1H, d, J=2.1 Hz, 6-H or 8-H), 6.91 (1H, s, ArNHCH), 8.23 (1H, d, J=7.2 Hz, NHCO).

Workup

  1. custom(5 min)
  2. washwashed with brine (50 ml)
  3. dry with materialbefore drying (Na2SO4)
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was redissolved in xylene (20 ml)
  6. temperatureThe mixture was heated
  7. stirringwith stirring, in an oil bath (80° C.) for 16h
  8. customThe precipitate was removed by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-70c6844a7c5043f0bfbc26fcfc782289
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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