Succinic anhydride → HCID 10250893, compound

HRID 2396606Notes

Reaction equation

HRID 2396606 reaction equation
[CH2:1]([O:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1>N1C=CC=CC=1>[CH2:1]([O:8][N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 10267278HCID 10267278, compound

Product 1

HCID 10250893HCID 10250893, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Pyridine (80 mL) was added to (7) (6.38 g, 20.7 mmol ) and succinic anhydride (3.11 g, 31.1 mmol ) and the reaction was heated under nitrogen at 80°-86° C. for 1.5 hours. Solvent was removed under high vacuum and the residue was dissolved with ether (150 mL) and washed with saturated NaHCO3 (4×50 mL). The aqueous portion was extracted with ether (2×50 mL), cooled to 0° C., acidified with cold 1N HCl (350 mL) and extracted with CHCl] (6×100 mL). A water wash (100 mL), solvent removal and flash column chromatography, eluting with 6% CH3OH/CH2Cl2, gave 7.46 g (88%) of (8) as a solid: mp 93°-94° C., NMR δ 1.2-1.8 (m+s, 16 H), 2.62 (s, 4 H), 2.9-3.2 (m, 2 H), 3.51-3.76 (m, 2 H), 4.8 (s, 2 H), 7.33 (s, 6 H). Anal. calcd. for C21H32N2O6 : C, 61.75; H, 7.90, N, 6.86. Found: C, 61.48; H, 7.90; N, 6.79.

Workup

  1. temperaturethe reaction was heated under nitrogen at 80°-86° C. for 1.5 hours
  2. customSolvent was removed under high vacuum
  3. dissolutionthe residue was dissolved with ether (150 mL)
  4. washwashed with saturated NaHCO3 (4×50 mL)
  5. extractionThe aqueous portion was extracted with ether (2×50 mL)
  6. extractionextracted with CHCl] (6×100 mL)
  7. washA water wash
  8. custom(100 mL), solvent removal and flash column chromatography
  9. washeluting with 6% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-44086f7d8261460f8081bc8728ec0539
Source dataset
uspto-grants-1996_02
Patent number
US05493053

Reaction notes

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