Water → (4Z)-5-bromo-4-[[(3-hydroxy-4-methoxyphenyl)methylamino]methylidene]isoquinoline-1,3-dione

HRID 2236608Notes

Reaction equation

HRID 2236608 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].CCN(CC)CC.[Br:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1/[C:23](=[CH:33]\OC)/[C:24](=[O:32])[NH:25][C:26]2=[O:31].O>CN(C)C=O>[Br:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1/[C:23](=[CH:33]/[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([OH:2])[CH:4]=1)/[C:24](=[O:32])[NH:25][C:26]2=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 162176463-Hydroxy-4-methoxybenzylamine hydrochlorideHCID 68696086(4E)-5-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178491079(4Z)-5-bromo-4-[[(3-hydroxy-4-methoxyphenyl)methylamino]methylidene]isoquinoline-1,3-dioneYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 88.5 mg (0.468 mmol) of 3-hydroxy-4-methoxy-benzylamine hydrogen chloride in 1.8 mL of N,N-dimethylformamide (DMF) at RT under N2 is treated with 94.5 mg (0.936 mmol) of Et3N. (4E)-5-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (132 mg, 0.468 mmol) is added and the mixture is stirred for 3.5 h. Water is added and the product is collected, washed with H2O and Et2O and dried to give 163 mg (86%) of pale yellow amorphous solid: mp 204-206° C.; 1H NMR (DMSO-d6) δ 11.11 (s, 1H), 10.56 (m, 1H), 9.08 (s, 1H), 8.93 (d, 1H, J=13.6 Hz), 8.05 (d, 1H, J=6.9 Hz), 7.87 (d, 1H, J=6.9 Hz), 7.09 (m, 1H), 6.91 (d, 1H, J=8.07 Hz), 6.78 (m, 2H), 4.49 (d, 2H, J=5.37 Hz), 3.75 (s, 3H); HRMS (ESI) m/z calcd for C18H15BrN2O4 403.02880. found 403.02840 (M+H)+1.

Workup

  1. customthe product is collected
  2. washwashed with H2O and Et2O
  3. customdried

Sources & evidence

ORD record
ord-3f59e7ee767a46a4a1b8bf5d10ab0267
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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