Dicyclohexylcarbodiimide → Succinimide 3,4-dihydrocarbostyril-6-carboxylate

HRID 2225319Notes

Reaction equation

HRID 2225319 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].C1(N=C=NC2CCCCC2)CCCCC1>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 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

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 containing 12.4 g of dicyclohexylcarbodiimide in 50 ml of dioxane was added dropwise thereto under ice-cooled condition with stirring. The reaction mixture was further stirred for 4 hours at 90° C. After the reaction was completed, the reaction mixture was allowed to stand to cool at room temperature, and the crystals precipitated were removed by filtration, then the filtrate obtained was concentrated to dryness. The residue was recrystallized from dimethylformamide-ethanol to obtain 10.8 g of succinimide 3,4-dihydrocarbostyril-6-carboxylate in the form of colorless flake-like crystals.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooled condition
  3. stirringThe reaction mixture was further stirred for 4 hours at 90° C
  4. customthe crystals precipitated
  5. customwere removed by filtration
  6. customthe filtrate obtained
  7. concentrationwas concentrated to dryness
  8. customThe residue was recrystallized from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-845e8608a68043979468873a6f2d8209
Source dataset
uspto-grants-1994_09
Patent number
USRE034722

Reaction notes

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