Ethyl acetate hexane → HCID 57949509, compound

HRID 2427760Notes

Reaction equation

HRID 2427760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH2:22])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)[CH2:7]2.[H][H].CCCCCC.C(OCC)(=O)C>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][CH3:22])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 67251387HCID 67251387, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57949509HCID 57949509, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-5-ethenyl-2-(4-ethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.062 g, 0.2 mmol) and 10% palladium on carbon (20 mg) in ethanol (25 mL) was reduced under 45 p.s.i. hydrogen. Workup and silica gel column chromatography using combinations 3:1 hexane-ethyl acetate afforded 7-chloro-5-ethyl-2-(4-ethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.031 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.23 (t, 6H), 2.68 (q, 4H), 4.18 (s, 2H), 4.72 (s, 2H), 7.07 (s, 1H), 7.14-7.36 (m, 5H). GC-MS: m/z 313 (M)+, 284 (M−29)+.

Sources & evidence

ORD record
ord-ee70dd438d304984bdac89eef05ec582
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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