Acetic Acid → HCID 12851866, compound

HRID 1156893Notes

Reaction equation

HRID 1156893 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15](CC#N)[C:14]=3[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23]([OH:26])(=[O:25])[CH3:24]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:24][C:23]([OH:26])=[O:25])[C:14]=3[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12851840HCID 12851840, compound

Product 1

HCID 12851866HCID 12851866, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1-(4-Nitrophenyl)isoquinoline-5-acetonitrile (2.1 g) was dissolved in 12 ml of 75% sulfuric acid and 2 ml of acetic acid, and refluxed for 3 hours. The reaction mixture was poured into ice water, and washed with ether. The aqueous layer was neutralized with an aqueous solution of sodium hydroxide. The crystals that precipitated were collected by filtration, and recrystallized from tetrahydrofuran to afford 2.1 g of 1-(4-nitrophenyl)isoquinoline-5-acetic acid having a melting point of 252.2° to 253.8° C.

Workup

  1. washwashed with ether
  2. customThe crystals that precipitated
  3. filtrationwere collected by filtration
  4. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-88029b9bf4d446f58e4a5b24c4a1dbb6
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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