Water → 2-Phthalimidomethylindoline

HRID 52466Notes

Reaction equation

HRID 52466 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1.[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.O>C1(C)C=CC=CC=1>[C:12]1(=[O:17])[N:1]([CH2:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4]2)[C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 218304062-Aminomethylindoline

Product 1

HCID 104462652-PhthalimidomethylindolineYield 105.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-aminomethylindoline (6.0 g, 40.48 mmol) and phthalic anhydride (6.30 g, 42.51 mmol) in toluene (600 mL) was refluxed for 4 h, while water generated during the reaction was removed by azeotropic distillation by using Dean-Stark apparatus. The mixture was concentrated to give a crude 2-phthalimidomethylindoline (11.84 g), which was used for the next step without further purification: 1H NMR (270 MHz, CDCl3) δ7.82 (m, 2H), 7.71 (m, 2H), 7.03 (d, 1H, J=7 Hz), 6.95 (dt, 1H, J=1,7 Hz), 6.61 (m, 2H), 4.19 (m, 1H), 3.86 (d, 2H, J=6 Hz), 3.18 (dd, 1H, J=16, 9 Hz), 2.93 (dd, 1H, J=16, 6 Hz).

Workup

  1. customwas removed by azeotropic distillation
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-8686a85b4f9044bbb2eee76a2c15f610
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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