5-Aminoisoquinoline → HCID 21436744, compound

HRID 2397927Notes

Reaction equation

HRID 2397927 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(=O)(O)[O-].[K+].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:22](Cl)=[O:23]>C1C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:22]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)=[O:23]

Participants

5

Reactant 3

HCID 707665-Aminoisoquinoline2×HCID 77070Veratroyl chlorideHCID 516893Potassium Bicarbonate

Product 1

HCID 21436744HCID 21436744, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Aminoisoquinoline (8 g.) was dissolved in dry benzene (100 ml) and 0.5 g of dry potassium bicarbonate was added to the solution. A 0.1 mole excess of 3,4-dimethoxybenzoyl chloride was dissolved in dry benzene (50 ml) and this solution was poured into the solution of 5-aminoisoquinoline. A precipitate formed immediately. This was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the insoluble residue was recrystallized from benzene to yield 11.5 g of 5-(3,4-dimethoxybenzamido)isoquinoline as tan needles, m.p. 193°-194° C.

Workup

  1. customA precipitate formed immediately
  2. filtrationThis was collected by filtration
  3. washwashed with 10% sodium carbonate solution
  4. customthe insoluble residue was recrystallized from benzene

Sources & evidence

ORD record
ord-2a51c18e53434e61859c71590771634f
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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