Methanol → 1026989-91-2

HRID 548792Notes

Reaction equation

HRID 548792 reaction equation
O.NN.[C:4]([O:8][CH2:9][CH2:10][CH2:11][O:12][N:13]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:7])([CH3:6])[CH3:5].CO>C(Cl)Cl>[C:4]([O:8][CH2:9][CH2:10][CH2:11][O:12][NH2:13])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 59774397HCID 59774397, compound

Product 1

HCID 592592441026989-91-2Yield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrazine hydrate (1.36 mL, 43.3 mmol) was added to a solution of 2-(3-tert-Butoxy-propoxy)-isoindole-1,3-dione (6.0 g, 21.7 mmol) in CH2Cl2 (50 mL) with MeOH (5 mL), and the reaction stirred 1 h at room temperature. The precipitate was removed by filtration, and the filtrate was purified by silica gel chromatography (6% MeOH/CH2Cl2) to give 2.4 g (75%) of compound 29A as a clear oil. 1H NMR (400 MHz, CDCl3): δ 4.94 (br s, 2H), 3.71 (t, 2H, J=6.4 Hz), 3.38 (t, 2H, J=6.4 Hz), 1.70-1.79 (m, 2H), 1.15 (s, 9H).

Workup

  1. customThe precipitate was removed by filtration
  2. customthe filtrate was purified by silica gel chromatography (6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-de8e1aaa0b0e45db9c0d2458ef45d967
Source dataset
uspto-grants-2011_05
Patent number
US07943626B2

Reaction notes

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