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Sodium Acetate → 1-(2'-Chlorophenyl)-1,4-dihydro-benz[g]isoquinol-3-one

HRID 1252706
Notes
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Reaction equation

HRID 1252706 reaction equation
Br[C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]2[C:3]=1[CH2:4][C:5](=[O:23])[NH:6][CH:7]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].C([O-])(=O)C.[Na+].[H][H]>C(O)(=O)C.[Pd]>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:7]1[C:8]2[C:3](=[CH:2][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH:9]=2)[CH2:4][C:5](=[O:23])[NH:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 20139029HCID 20139029, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 201390301-(2'-Chlorophenyl)-1,4-dihydro-benz[g]isoquinol-3-oneYield 76.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 176
Acetic Acid
Solvent

Procedure

A mixture of 5-bromo-1-(2'-chlorophenyl)-1,4-dihydrobenz[g]isoquinol-3-one (Description 7) (7.6 g), sodium acetate (3.0 g) and 10% palladium-charcoal (2.0 g) in acetic acid (750 ml) was hydrogenated at atmospheric temperature and pressure until the initial rapid uptake of hydrogen had ceased (2.5 hours). The mixture was filtered (celite) and the filtrate evaporated to dryness in vacuo and recrystallised from ethylacetate to afford the title compound (4.65 g) m.p. 234°-237° C.

Workup

  1. custom(2.5 hours)
  2. filtrationThe mixture was filtered (celite)
  3. customthe filtrate evaporated to dryness in vacuo
  4. customrecrystallised from ethylacetate

Sources & evidence

ORD record
ord-1dcea01611334319a222f252ea401396
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04745115

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes