Water → 7H-1,3-Benzodioxolo[4,5-f]isoindole-7,9(8H)-dione, 10-(1,3-benzodioxol-5-yl)-8-(3-hydroxypropyl)-

HRID 2354600Notes

Reaction equation

HRID 2354600 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[C:16]4[C:30](=O)[O:29][C:28](=[O:32])[C:17]=4[CH:18]=[C:19]4[C:27]=3[C:23]3[O:24][CH2:25][O:26][C:22]=3[CH:21]=[CH:20]4)=[CH:14][C:9]=2[O:8][CH2:7]1.O>C1(C)C=CC=CC=1>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[C:27]4[C:19](=[CH:20][CH:21]=[C:22]5[O:26][CH2:25][O:24][C:23]5=4)[CH:18]=[C:17]4[C:28](=[O:32])[N:1]([CH2:2][CH2:3][CH2:4][OH:5])[C:30](=[O:29])[C:16]=34)=[CH:14][C:9]=2[O:8][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 90863-Amino-1-propanolHCID 527377710-Benzo[1,3]dioxol-5-yl-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione

Product 1

HCID 52738027H-1,3-Benzodioxolo[4,5-f]isoindole-7,9(8H)-dione, 10-(1,3-benzodioxol-5-yl)-8-(3-hydroxypropyl)-Yield 11%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-Amino-1-propanol (27 mg, 0.36 mmol) in toluene (5 mL) at 0° C. was added dropwise to a stirred solution of anhydride 1 (109 mg, 0.3 mmol) in toluene (40 mL). The mixture was stirred at room temperature for 1 h and then heated under Dean-Stark trap for 3 h. After water ceased to distill, the reaction mixture was cooled, washed successively with water (2×50 mL), 5% aqueous NaHCO3 solution (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed in vacuo, and the resulting product was purified by column chromatography on silica gel using CH2Cl2/acetone (3:1 to 1:1, v/v) to provide 29 (10 mg, 11%) as a pale yellow powder. mp 150-152° C.; 1H NMR (CDCl3) δ 8.27 (s, 1H, H4), 7.56 (d, 1H, H5, J=8.4 Hz), 7.26 (d, 1H, H6, J=8.4 Hz), 6.86-6.91 (m, 3H, H2′+H5′+H6′), 6.04 (s, 2H, 3′,4′-OCH2O—), 5.97 (s, 2H, 7,8-OCH2O—), 3.69-3.76 (m, 4H, NCH2CH2CH2OH), 1.83 (m, 2H, NCH2CH2CH2OH).

Workup

  1. temperatureheated under Dean-Stark trap for 3 h
  2. distillationto distill
  3. temperaturethe reaction mixture was cooled
  4. washwashed successively with water (2×50 mL), 5% aqueous NaHCO3 solution (2×50 mL), and water (2×50 mL)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe resulting product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0c436386295c44839600afe97040ec9a
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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