4-Aminocatechol → HCID 178518331, compound

HRID 2236920Notes

Reaction equation

HRID 2236920 reaction equation
CO[CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][C:5]1=[O:15].[OH:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[OH:24])[NH2:20]>CN(C)C=O>[OH:16][C:17]1[CH:18]=[C:19]([NH:20][CH:3]=[C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[NH:6][C:5]2=[O:15])[CH:21]=[CH:22][C:23]=1[OH:24]

Participants

4

Reactant 2

HCID 1517264-AminocatecholHCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178518331HCID 178518331, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
115 °C

Procedure

To a suspension of 4-Methoxymethylene-4H-isoquinoline-1,3-dione (40.6 mg, 0.2 mmol) in N,N-dimethylformamide (0.5 mL) is added 3,4-dihydroxyaniline (25 mg, 0.2 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. The reaction mixture is diluted to 2 mL with N,N-dimethylformamide and purified by C18 reverse phase HPLC. The pure fractions were combined and concentrated to yield the title compound (15.6 mg).

Workup

  1. custompurified by C18 reverse phase HPLC
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ef615b3ac6004c3f8c4cabdd00a07a56
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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