4-Methoxybenzylamine → HCID 20481285, compound

HRID 1648886Notes

Reaction equation

HRID 1648886 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[ClH:11].NCCC1C=CC(OC)=C2C=1[CH2:17][C:18](=[O:26])[NH:19]2>>[ClH:11].[NH2:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]2[C:5]=1[CH2:17][C:18](=[O:26])[NH:19]2

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 20481280HCID 20481280, compound

Product 1

HCID 20481285HCID 20481285, compound

Procedure

Using 65 g of p-methoxybenzylamine for the starting material of Example 1 gives 4-aminomethyl-7-methoxy-2(3H)-indolone hydrochloride. This material (2 g) was converted to the base and alkylated using 1 mole equivalent of isovaleraldehyde as in Example 2 to give 4-isopentylaminomethyl-7-methoxy-2(3H)-indolone hydrobromide and 4-isopentylaminomethyl-7-hydroxy-2(3H)-indolone hydrobromide after demethylation using boron tribromide in methylene chloride at -20°.

Sources & evidence

ORD record
ord-6a83a1ab683f4f6089b0cda50add3e47
Source dataset
uspto-grants-1983_11
Patent number
US04414224

Reaction notes

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