O-Methylhydroxylamine hydrochloride → (4Z)-6-(3-Furyl)-4-{[(3-hydroxy-4,5-dimethoxybenzyl)amino)methylene}isoquinoline

HRID 2236610Notes

Reaction equation

HRID 2236610 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].CO[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1OC)[C:22](=O)[NH:21][C:20](=O)/[C:19]/2=[CH:30]/OC.Cl.OC1C=C([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])CN.Cl.CON>>[O:43]1[CH:42]=[CH:41][C:40]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[N:21][CH2:20]/[C:19]/3=[CH:30]\[NH:6][CH2:5][C:4]2[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:2]([OH:1])[CH:3]=2)=[CH:44]1

Participants

5

Reactant 4

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 162176463-Hydroxy-4-methoxybenzylamine hydrochlorideHCID 68694177HCID 68694177, compoundHCID 68696006(4E)-6,7-dimethoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 86619581(4Z)-6-(3-Furyl)-4-{[(3-hydroxy-4,5-dimethoxybenzyl)amino)methylene}isoquinoline

Procedure

Using the procedure described for the preparation of example 46, 120 mg of brown solid (50%) yield is obtained from 150 mg (0.57 mmol) of (4E)-6-(3-furyl)methoxymethylene-isoquinoline-1,3(2H,4H-dione, (prepared similarly to 4-methoxymethylene-6-thiophin-3-yl-isoquinolin-(4H)-1,3-dione) and 3-hydroxy-4,5-dimethoxybenzylamine (115 mg, 0.57 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 263-264° C.

Sources & evidence

ORD record
ord-04f9591e5b754ffc9fd9690d0045cf9f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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