Methanol → 3-Methoxy-3-(1-ethyl-2-methylindol-3-yl)phthalide

HRID 1789276Notes

Reaction equation

HRID 1789276 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[O:13])=[C:4]1[CH3:23])[CH3:2].S(Cl)(Cl)=O.CO.N1C=CC=C[CH:31]=1>C(Cl)CCl>[CH3:31][O:13][C:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:1][CH3:2])[C:4]=2[CH3:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:18])[O:17]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-

Product 1

HCID 139315033-Methoxy-3-(1-ethyl-2-methylindol-3-yl)phthalide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Proceeding in a manner similar to that described in Example 1 above, 5.1 g of 2-(1-ethyl-2-methylindol-3-yl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of pyridine to obtain 2.1 g of 3-methoxy-3-(1-ethyl-2-methylindol-3-yl)phthalide (Formula III: R0 =R=R1 =R2 =R8 =H; R6 =C2H5 ; R7 =Y=CH3 ; X=O), a dark brown-colored oil. Significant infrared maxima appeared at 1770 (C=O; s) and 740 cm-1 (C=O; s). Analysis by mass spectrum showed m/e peaks at 321 (M+) and 290 (M+ -OCH3). A toluene solution of the product spotted on an acidic clay-coated paper developed a red-purple-colored image.

Sources & evidence

ORD record
ord-e9cef888cfe447b9a68601f054b7153b
Source dataset
uspto-grants-1987_08
Patent number
US04688059

Reaction notes

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