4-Aminobenzyl alcohol → HCID 178518327, compound

HRID 2236914Notes

Reaction equation

HRID 2236914 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].[NH2:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1>CN(C)C=O>[OH:22][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([NH:16][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:18][CH:19]=1

Participants

4

Reactant 2

HCID 693314-Aminobenzyl alcoholHCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178518327HCID 178518327, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of 4-Methoxymethylene-4H-isoquinoline-1,3-dione (203 mg, 1.0 mmol) in N,N-dimethylformamide (2.5 mL) is added 4-aminobenzyl alcohol (123.2 mg, 1.0 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. Upon cooling to ambient temperature, product precipitated out of solution. The product is recovered by filtration, rinsing with diethyl ether, and drying to yield 263.3 mg 4-[(4-Hydroxymethyl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione.

Workup

  1. temperatureUpon cooling to ambient temperature
  2. customproduct precipitated out of solution
  3. filtrationThe product is recovered by filtration
  4. washrinsing with diethyl ether
  5. customdrying

Sources & evidence

ORD record
ord-b4626bdeb00741ddb21d4fb70bd7aff4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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