Acetic Acid → HCID 69157050, compound

HRID 750154Notes

Reaction equation

HRID 750154 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].C(O)(=O)C.C([O-])(=O)C.[Na+].[Br:42]Br>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[C:32]([Br:42])=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408Bromine3×HCID 517045Sodium Acetate2×HCID 10239063HCID 10239063, compound

Product 1

HCID 69157050HCID 69157050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg) in THF (6 ml) were added acetic acid (3 ml) and sodium acetate (100 mg) at room temperature, and bromine (0.04 ml) was added dropwise under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr., sodium acetate (100 mg) was added, and bromine (0.04 ml) was added dropwise at room temperature. The reaction mixture was further stirred at room temperature for 1 hr., and bromine (0.04 ml) was added dropwise. The mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue and crystals were collected by filtration. The crystals were further washed with ethyl acetate to give the title compound (250 mg).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at room temperature for 1 hr
  3. stirringThe mixture was stirred for 1 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure, water
  5. additionwas added to the residue and crystals
  6. filtrationwere collected by filtration
  7. washThe crystals were further washed with ethyl acetate

Sources & evidence

ORD record
ord-4763515993964d5c80b6c3661e98a086
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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