ChemicalBook CAS DataBase List 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE

5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE synthesis

4synthesis methods

Product Name:5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE
CAS Number:127168-88-1
Molecular formula:C9H11NO
Molecular Weight:149.19

50727-04-3 Synthesis

50727-04-3
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$23.00/100mg

127168-88-1
109 suppliers
$70.00/100mg

Yield: 47%

Reaction Conditions:

Stage #1:4-methoxyphthalimide with borane-THF in tetrahydrofuran at 0; for 16 h;Heating / reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran;methanol;water for 3 h;Heating / reflux;

Steps:

C.C2
A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at 0⁰C was treated dropwise with a solution of borane in tetrahydrofuran (1M₁ 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to 0⁰C, methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3 x 750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. ¹H NMR (DMSOd₆) 7.13 (1 H₁ d), 6.84 (1H, d), 6.74 (1H₁ dd), 4.05 (2H, s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]⁺ 150.

References:

ASTEX THERAPEUTICS LIMITED WO2008/44029, 2008, A1 Location in patent:Page/Page column 204