Succinic anhydride → HCID 25030431, compound

HRID 250789Notes

Reaction equation

HRID 250789 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)=[C:17]([O:29]CC3C=CC=CC=3)[CH:16]=1)=[C:9]([OH:37])[C:8]2=[O:38])(=[O:3])[CH3:2].C1(=O)[O:44][C:42](=[O:43])[CH2:41]C1>Cl.C(O)(=O)C.O.N1C=CC=CC=1>[OH:29][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[OH:21])[C:10]1[O:11][C:12]2[C:7]([C:8](=[O:38])[C:9]=1[OH:37])=[CH:6][C:5]([NH:4][C:1]([CH2:2][CH2:41][C:42]([OH:44])=[O:43])=[O:3])=[CH:14][CH:13]=2

Participants

7

Reactant 2

HCID 7922Succinic anhydrideHCID 69321477HCID 69321477, compound

Product 1

HCID 25030431HCID 25030431, compoundYield 19%

Reagents, catalysts & solvents 4

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

Procedure

A mixture of the protected flavonol (15) (500 mg, 0.985 mmol) in aqueous HCl (36%, 37 mL) and acetic acid (37 mL) was heated under reflux for 3 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 (322 mg). A mixture of the crude yellow product and succinic anhydride (118 mg, 1.18 mmol) in pyridine was stirred at room temperature for 4 h. Water (1 mL) was added and the mixture was acidified with 6 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 (3) as a yellow powder (70.0 mg, 19%), m.p 257-258° C. 1H NMR (399.7 MHz, d6-DMSO) δ 2.54-2.60 (m, 4H, CH2CH2); 6.89 (d, 1H, J5′,6′ 8.5 Hz, H5′); 7.57 (dd, 1H, J2′,6′ 2.5, J5′,6′ 8.5 Hz, H6′); 7.66 (d, 1H, J7,8 9 Hz, H8); 7.73 (d, 1H, J2′,6′ 2.5 Hz, H2′); 7.85 (dd, 1H, J5,7 2.5, J7,8 9.0 Hz, H7); 8.43 (d, 1H, J5,7 2.5 Hz, H5); 9.29, 9.32, 9.59 (3 br s, 3×1H, 3×OH); 10.29 (s, 1H, NH); 12.20 (br s, 1H, CO2H). 13C NMR (100.5 MHz, d6-DMSO) δ 28.83, 31.11 (2C, CH2CH2); 112.7, 115.25, 115.65, 118.76, 120.00, 121.43, 122.39, 125.17, 135.80, 137.67, 145.12, 146.04, 147.63, 150.38 (14C, Ar); 170.46, 172.32, 173.93 (3C, 3×C═O). Low resolution mass spectrum (ESI) m/z 384.4 [C19H15NO8 (M-H)+ requires 384.08].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 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 (322 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-fa34f76195614d9bb9db8ad14fb8955b
Source dataset
uspto-grants-2011_01
Patent number
US07863323B1

Reaction notes

Loading…