N-Hydroxysuccinimide → Succinimide 3,4-dihydrocarbostyril-6-carboxylate

HRID 358482Notes

Reaction equation

HRID 358482 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([OH:3])=[O:2].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].ClC(Cl)CCCCCN=C=N>O1CCOCC1>[NH:10]1[C:11]2[C:6](=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14].[C:17]1(=[O:22])[NH:16][C:20](=[O:21])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acidHCID 71510291Dichlorohexylcarbodiimide

Product 1

HCID 19003899Succinimide 3,4-dihydrocarbostyril-6-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

10 Grams of 6-carboxy-3,4-dihydrocarbostyril and 6.0 g of N-hydroxysuccinimide were suspended in 200 ml of dioxane. Then a solution of 12.4 g of dichlorohexylcarbodiimide in 50 ml of dioxane was added drop-wise of the suspension under ice-cooling with stirring. The reaction mixture was heated at 90° C. for 4 hours. After the reaction was completed, the reaction mixture was cooled to a room temperature, and the crystals being precipitated were removed by filtration and the mother liquor was concentrated by distillation. The residue was recrystallized from dimethylformamide-ethanol to obtain 10.8 g of succinimide 3,4-dihydrocarbostyril-6-carboxylate. Melting point: 234.5°-236° C. Colorless flake-like crystals.

Workup

  1. temperaturecooling
  2. temperaturethe reaction mixture was cooled to a room temperature
  3. customthe crystals being precipitated
  4. customwere removed by filtration
  5. concentrationthe mother liquor was concentrated by distillation
  6. customThe residue was recrystallized from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-e437fbe62591435b80a8b2b3d853141f
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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