Water → HCID 15595974, compound

HRID 1200258Notes

Reaction equation

HRID 1200258 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:20](=[O:21])[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]2=[O:22])=[C:4]([F:23])[CH:3]=1.[N:24]([O-])=O.[Na+].O>C(O)(=O)C>[F:23][C:4]1[C:5]([N:12]2[C:13](=[O:22])[C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[C:20]2=[O:21])=[CH:6][C:7]2[N:8]([CH2:9][C:10]#[CH:11])[N:24]=[N:1][C:2]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15595972HCID 15595972, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15595974HCID 15595974, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[4-Amino-2-fluoro-5-(2-propynylamino)phenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.59 g) was dissolved in acetic acid (1.9 ml), and sodium nitrite (0.13 g) was added thereto at a temperature of 10° to 15° C. After stirring for 10 minutes, the reaction mixture was admixed with water and extracted with ethyl acetate. The extract was washed with water and an aqueous solution of sodium bicarbonate, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and hexane (1:2 by volume) as an eluent to give 2-[5-fluoro-1-(2-propynyl)benzotriazol-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.07 g) as a resinous material.

Workup

  1. customat a temperature of 10° to 15° C
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialan aqueous solution of sodium bicarbonate, dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel thin layer chromatography
  7. additiona mixture of ethyl acetate and hexane (1:2 by volume) as an eluent

Sources & evidence

ORD record
ord-ec170f04d5774066b0388afc0a5bc508
Source dataset
uspto-grants-1990_02
Patent number
US04904800

Reaction notes

Loading…