Succinic anhydride → HCID 58089059, compound

HRID 250787Notes

Reaction equation

HRID 250787 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][CH:16]=1)=[C:9]([OH:29])[C:8]2=[O:30])(=[O:3])[CH3:2].C1(=O)[O:36][C:34](=[O:35])[CH2:33]C1>Cl.C(O)(=O)C.O.N1C=CC=CC=1>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[O:11][C:12]3[C:7]([C:8](=[O:30])[C:9]=2[OH:29])=[CH:6][C:5]([NH:4][C:1]([CH2:2][CH2:33][C:34]([OH:36])=[O:35])=[O:3])=[CH:14][CH:13]=3)=[CH:20][CH:19]=1

Participants

7

Reactant 2

HCID 7922Succinic anhydrideHCID 66900418HCID 66900418, compound

Product 1

HCID 58089059HCID 58089059, compoundYield 38.3%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A mixture of the protected flavonol (11) (600 mg, 1.49 mmol) in aqueous HCl (36%, 38 mL) and acetic acid (38 mL) was heated under reflux for 2 h. The mixture was then cooled on ice and diluted with water. The resulting suspension was centrifuged and the collected solid washed with water, then freeze-dried to afford the salt as a crude yellow solid (457 mg). A mixture of the crude yellow product and succinic anhydride (179 mg, 1.79 mmol) in pyridine was stirred at room temperature for 4 h. Water (1 mL) was added and the mixture was acidified with 2 M HCl. The mixture was left to stand at room temperature for 30 min, and the resulting suspension was centrifuged and the collected solid was washed with water, freeze-dried and recrystallised from DMF/water to afford the succinamic acid (2) as a brown powder (211 mg, 38.2%), m.p. 256-257° C. Anal. Calcd. for C19H16NO7.½H2O: C, 60.32; H, 4.26; N, 3.70. Found: C, 59.99; H, 4.53; N, 3.90. 1H NMR (399.7 MHz, d6-DMSO) δ 2.55-2.60 (m, 4H, CH2CH2); 6.93 (app. d, 2H, J=9.2 Hz, H3′,5′); 7.69 (d, 1H, J7,8 8.8 Hz, H8); 7.85 (dd, 1H, J5,7 2.8, J7,8 8.8 Hz, H7); 8.09 (app. d, 2H, J=9.2 Hz, H2′,6′); 8.43 (d, 1H, J5, 7 2.8 Hz, H5); 9.33 (s, 1H, NH); 10.11, 10.31 (2 br s, 2×1H, 2×OH); 12.21 (br s, 1H, CO2H). 13C NMR (100.5 MHz, d6-DMSO) δ 25.16, 28.78 (2C, CH2CH2); 31.06, 67.05, 112.65, 115.46, 118.80, 121.45, 122.06, 125.11, 129.55, 135.80, 137.57, 146.01, 150.38, 159.11 (14C, Ar); 170.40, 172.33, 173.86 (3C, 3×C═O).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe mixture was then cooled on ice
  4. washthe collected solid washed with water
  5. customfreeze-dried
  6. customto afford the salt as a crude yellow solid (457 mg)
  7. waitThe mixture was left
  8. waitto stand at room temperature for 30 min
  9. washthe collected solid was washed with water
  10. customfreeze-dried
  11. customrecrystallised from DMF/water

Sources & evidence

ORD record
ord-969f5811ff1946c89dd3ba9ddb7e4be7
Source dataset
uspto-grants-2011_01
Patent number
US07863323B1

Reaction notes

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