Triethylamine → HCID 178419745, compound

HRID 2236932Notes

Reaction equation

HRID 2236932 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14]OC.Br.[OH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[OH:27])[CH2:22][NH2:23].C(N(CC)CC)C>CN(C)C=O>[BrH:1].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:26]([OH:27])=[C:19]([OH:18])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133435624-(Aminomethyl)benzene-1,2-diol--hydrogen bromide (1/1)HCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178419745HCID 178419745, compoundYield 195.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of crude 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (846 mg, 3 mmol) in N,N-dimethylformamide (7.5 mL) is added 3,4-dihydroxy benzylamine hydrobromide (660 mg, 3 mmol) and triethylamine (630 μL, 4.5 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. Upon cooling to room temperature, the product precipitated out. The precipitate is then filtered off, rinsed with copious amounts of ether, and dried to yield 1.38 g of 6-Bromo-4-[(3,4-dihydroxy-benzylamino)-methylene]-4H-isoquinoline-1,3-dione hydrobromide.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe product precipitated out
  3. filtrationThe precipitate is then filtered off
  4. washrinsed with copious amounts of ether
  5. customdried

Sources & evidence

ORD record
ord-ef5cc7bff6d94c758ce1b87bdd2f7b42
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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