O-Methylhydroxylamine hydrochloride → (4Z)-4-{[(3-Hydroxy-4,5-dimethoxybenzyl)amino)methylene}-6-phenylisoquinoline

HRID 2236609Notes

Reaction equation

HRID 2236609 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1OC)[C:9](=O)[NH:8][C:7](=O)/[C:6]/2=[CH:17]/OC.Cl.[OH:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:25][NH2:26].Cl.[CH3:33][O:34]N>>[OH:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([O:34][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:25][NH:26]/[CH:17]=[C:6]1\[CH2:7][N:8]=[CH:9][C:10]2[C:5]\1=[CH:4][C:3]([C:3]1[CH:4]=[CH:5][CH:10]=[CH:11][CH:12]=1)=[CH:12][CH:11]=2

Participants

4

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 162176463-Hydroxy-4-methoxybenzylamine hydrochlorideHCID 68696006(4E)-6,7-dimethoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 86619580(4Z)-4-{[(3-Hydroxy-4,5-dimethoxybenzyl)amino)methylene}-6-phenylisoquinoline

Procedure

Using the procedure described for the preparation of example 46, 50 mg of orange solid (40% yield) is obtained from 80 mg (0.29 mmol) of 4-methoxymethylene-6-phenyl-3-yl-isoquinolin-(4H)-1,3-dione and 3-hydroxy-4,5-dimethoxybenzylamine 115 mg (0.29 mmol), (prepared similarly to (4E)-6,7-dimethoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione and 3-hydroxy-4-methoxy-benzylamine hydrogen chloride, except methoxy amine hydrogen chloride is used instead of hydroxylamine hydrogen chloride); mp 250-251° C.

Sources & evidence

ORD record
ord-a465c566b596419bbd7d326c12f90c9f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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