HCID 53380668, compound → HCID 67404004, compound

HRID 333677Notes

Reaction equation

HRID 333677 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 53380668HCID 53380668, compound

Product 1

HCID 67404004HCID 67404004, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
140 °C

Procedure

The compound 7-methoxy-3-(4-methoxyphenyl)isoquinoline-1(2H)-one (300 mg, 1 mmol), benzyltriethylammonium chloride (1.68 g, 7 mmol) and 37% hydrochloric acid (20 mL) are introduced into a sealed tube. The medium is heated for 20 hours at 140° C. then the mixture is evaporated to dryness under reduced pressure. After the addition of water (20 mL) to the residue obtained, a precipitate is formed. It is filtered and dried under in order to produce the expected 7-hydroxy-3-(4-hydroxyphenyl)isoquinoline-1(2H)-one 57 (200 mg, 74%) in the form of a brown solid.

Workup

  1. customthe mixture is evaporated to dryness under reduced pressure
  2. additionAfter the addition of water (20 mL) to the residue
  3. customobtained
  4. customa precipitate is formed
  5. filtrationIt is filtered
  6. customdried under in order

Sources & evidence

ORD record
ord-15e05c145c45456aad98151a904f9f50
Source dataset
uspto-grants-2014_11
Patent number
US08883763B2

Reaction notes

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