Phthalic Anhydride → HCID 67690982, compound

HRID 484457Notes

Reaction equation

HRID 484457 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][C:10]=2[Cl:12])[NH:5][C@@H:4]([C:14]([O:16]C)=[O:15])[CH2:3]1.C(N(CC)CC)C.[C:25]1(=[O:35])[O:30][C:28](=[O:29])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12>O1CCCC1.CN(C)C1C=CN=CC=1>[C:28]([C:27]1[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=1[C:25]([NH:1][C@@H:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][C:10]=2[Cl:12])[NH:5][C@@H:4]([C:14]([OH:16])=[O:15])[CH2:3]1)=[O:35])([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 10968967HCID 10968967, compound

Product 1

HCID 67690982HCID 67690982, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (0.5 g, 1.6 mmol) in anhydrous tetrahydrofuran (50 ml) under an atmosphere of nitrogen was added dry triethylamine (0.49 ml, 3.5 mmol) and the mixture stirred until dissolution was complete. To this solution was added phthalic anhydride (0.28 g, 1.9 mmol) and 4-dimethylaminopyridine (5 mg) and the reaction mixture was stirred at room temperature for 3 hours. The mixture was then evaporated to dryness in vacuo and the residue was partitioned between ethyl acetate (100 ml) and water (200 ml). The organic layer was separated and washed successively with dilute hydrochloric acid (2×50 ml, 1M), water (1×50 ml) and brine (1×50 ml), then dried (MgSO4) and evaporated to give a solid which was recrystallised from ethyl acetate/hexane to give the title compound as colourless crystals (0.45 g), m.p. 241°-243° C.; δ (360 MHz, DMSO) 1.71 (1H, ddd, J=13.0, 12.5 and 4.1 Hz, CHACHBHCCHD), 2.45 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 3.74 (3H, dd, J=12.6 and 4.1 Hz, CHACHBHCCHD), 5.19 (1H, m, CHACHBHCCHD), 6.68 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.82 (1H, s, ArNH), 6.84 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.54 (4H, m, ArH), 8.64 (1H, d, J=7.0 Hz, CHDNHCOCH2), 12.86 (1H, bs, CO2H); m/e (FAB+) 423 (M+1).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3 hours
  2. customThe mixture was then evaporated to dryness in vacuo
  3. customthe residue was partitioned between ethyl acetate (100 ml) and water (200 ml)
  4. customThe organic layer was separated
  5. washwashed successively with dilute hydrochloric acid (2×50 ml, 1M), water (1×50 ml) and brine (1×50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ea32c0094e9547bbb9e123ce752af859
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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