Water → HCID 178518275, compound

HRID 2236597Notes

Reaction equation

HRID 2236597 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH2:5][NH2:6].C(N(CC)CC)C.[Br:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[NH:24][C:23](=[O:30])/[C:22]/2=[CH:31]/OC.O>CN(C)C=O>[Br:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[NH:24][C:23](=[O:30])/[C:22]/2=[CH:31]\[NH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([OH:10])=[C:2]([OH:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 91623DihydroxybenzylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178518275HCID 178518275, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to general procedure 1, an amount of 3, 4 dihydroxybenzylamine (0.596 g, 4.3 mmol), is dissolved in N,N-dimethylformamide (61 mL). 1.8 ml (12.9 mmol) of triethylamine is added followed by 1.21 g (4.3 mmol) of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione. After the mixture is stirred at room temperature for 30 min, water (5 mL) is added and the reaction mixture is stirred for 60 min. The precipitate is filtered and washed several times with anhydrous ether. The crude solid is then purified by high performance liquid chromatography to give 910 mg of a white solid. MS (ESI) m/z 389.7 (M+1).

Workup

  1. stirringthe reaction mixture is stirred for 60 min
  2. filtrationThe precipitate is filtered
  3. washwashed several times with anhydrous ether
  4. customThe crude solid is then purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-ff29bf10ff054da5b7ded7482f32fee4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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