Potassium Hydroxide → Phthalimide

HRID 2220823Notes

Reaction equation

HRID 2220823 reaction equation
C1C(C2C(=O)C3C=CC(O)=CC=3OC=2)=CC=C(O)C=1.[OH-].[K+].BrCCCC[N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37]>CC(C)=O>[C:31]1(=[O:32])[NH:27][C:28](=[O:37])[C:29]2=[CH:36][CH:35]=[CH:34][CH:33]=[C:30]12

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 93575N-(4-Bromobutyl)phthalimideHCID 5281708Daidzein

Product 1

HCID 6809PhthalimideYield 33.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 5.3 g of daidzein (20.85 mmol) and 50 ml of acetone, 11 ml of 2 N KOH (22 mmol) and 5.6 g of N-(4-bromobutyl)-phthalimide (19.9 mmol) were added. The mixture was stirred under gentle reflux for 72 hours and concentrated. The residue was dissolved in chloroform-methanol (7:3) and loaded onto a Sephadex LH-20 column (chloroform:methanol, 7:3). Fractions that contained pure product were pooled, concentrated, and recrystallized from acetone to give 1.76 g of analog 13, a yield of 33.2% (w/w): mp 195-197° C. 1H NMR (DMSO-d6) δ 1.78 (—CH2—CH2—), 3.65 (—N—CH2—), 4.13 (—O—CH2—), 6.81 (d, 2H, J=8.5 Hz, 3′, 5′-H), 7.01 (dd, IH, J=8.89, 2.5 Hz, 6-H), 7.07 (d, IH, J=2.2 Hz, 8-H), 7.39 (d, 2H, J=8.6 Hz, 2′, 61-H), 7.80 (m, 2H, 5″, 6″-H), 7.83 (m, 2H, 4″, 7″-H), 7.96 (d, IH, J=8.89 Hz, 5-H), 8.32 (s, 1H, 2-H), 9.54 (s, 1H, 4′OH). 13C NMR (DMSO-d6) δ 24.6 (—CH2—), 25.8 (—CH2—), 37.1 (—N—CH2—), 67.9 (—CH2—O), 101.0 (C-8), 114.8 (C-6), 114.9 (C-3′, 5′), 117.5 (C-10), 122.4 (C-1′), 122.9 (C-3″, 8″), 123.6 (C-3), 126.9 (C-5), 130.0 (C-2′, 6′), 131.6 (C-5″, 6″), 134.3 (C-4″, 7″), 153.0 (C-2), 157.2 (C-9), 157.3 (C-4′), 162.8 (C-7), 168.0 (C-2″, 9″), 174.6 (C-4). MS (m/z) 456.5 (M+H)+. Anal. (C27H21O6N) for C, H, N. Cacld: 71.20, 4.65, 3.08; found: 70.89, 4.61, 3.09.

Workup

  1. additionwere added
  2. temperatureunder gentle reflux for 72 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in chloroform-methanol (7:3)
  5. concentrationconcentrated
  6. customrecrystallized from acetone
  7. customto give 1.76 g of analog 13

Sources & evidence

ORD record
ord-b58a8d01673a4eb9b2746a708bc12139
Source dataset
uspto-grants-2008_05
Patent number
US07368434B2

Reaction notes

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