Water → HCID 15595974, compound

HRID 844919Notes

Reaction equation

HRID 844919 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-8d8a625e3f0142d8b329b00d56b8b7a9
Source dataset
uspto-grants-1988_07
Patent number
US04755215

Reaction notes

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