Acetic Acid → HCID 12851862, compound

HRID 1156873Notes

Reaction equation

HRID 1156873 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13](CC#N)[C:12]=3[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:21]([OH:24])(=[O:23])[CH3:22].S(=O)(=O)(O)O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:22][C:21]([OH:24])=[O:23])[C:12]=3[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 128518341-(4-Bromophenyl)isoquinoline-5-acetonitrile

Product 1

HCID 12851862HCID 12851862, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.5 g of 1-(4-bromophenyl)isoquinoline-5-acetonitrile, 70 ml of acetic acid and 35 ml of 50% sulfuric acid was heated with stirring for 3 hours. After the reaction, water was added, and the pH of the reaction mixture was adjusted to 2 with an aqueous solution of sodium hydroxide. The crystals that precipitated were collected by filtration, and recrystallized from tetrahydrofuran-acetone to afford 7.0 g of 1-(4-bromophenyl)isoquinoline-5-acetic acid having a melting point of 230.5° to 232.5° C.

Workup

  1. temperaturewas heated
  2. additionwas added
  3. customThe crystals that precipitated
  4. filtrationwere collected by filtration
  5. customrecrystallized from tetrahydrofuran-acetone

Sources & evidence

ORD record
ord-97039894d1a541a784e6d002945d4c1c
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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