Isatin → 1-Allylisatin

HRID 71046

Reaction equation

HRID 71046 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[CH2:12](Cl)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7054IsatinHCID 7850Allyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 17135631-Allylisatin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A 500 mL flask is charged with isatin (50 g, 339 mmol), allyl chloride (33.8 g, 441 mmol), potassium carbonate (93.9 g, 679 mmol), and DMF (100 mL). The mixture is stirred at 70° C. for 14 hours (complete conversion by TLC), and then diluted with DMF. After filtration over a pad of cellite and removal of the solvent, the product remained as red crystals (68 g) which are used directly in the next step. 1HNMR (CDCl3, 300 MHz) δ 4.34 (dtr, 1H, 3J=5.3 Hz, 4J=1.8 Hz, NCH2CHC═CH2); 5.27 (dm, 1H, 3J=10.3 Hz, NCH2CHC═CHcis); 5.30 (dm, 1H, 3J=17.0 Hz, NCH2CHC═CHtrans); 5.82 (ddtr, NCH2CHC═CH2); 6.87 (d, 1H, 3J=7.9 Hz, H-7); 7.09 (br tr, 1H, 3J=7.3 Hz, H-5); 7.55 (dtr, 1H, 3J=8 Hz, H-6); 7.57 (d m, 1H, 3J=7.3 Hz, H-4). 13C-NMR (CDCl3, 75 MHz) δ 42.82 (NCH2); 111.11 (C-7); 117.77 (C-9); 118.80 (CH═CH2); 123.96 (C-5); 125.50 (C-4); 130.51 (CH═CH2); 138.48 (C-6); 150.96 (C-8); 158.02 (C-2); 183.29 (C-3).

Workup

  1. filtrationAfter filtration
  2. customover a pad of cellite and removal of the solvent

Sources & evidence

ORD record
ord-ef13f7fe59b6436297e671cc607c109d
Source dataset
uspto-grants-2014_09
Patent number
US08822702B2

Linked notes

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