O-Phenylenediamine → 1097816-83-5

HRID 2064594Notes

Reaction equation

HRID 2064594 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18](O)=O)=[N:10]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:18]1[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:9][N:10]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 78250Indazole-3-carboxylic acid

Product 1

HCID 1354644911097816-83-5Yield 45.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 1,2-diaminobenzene (108 mg), indazole-3-carboxylic acid (118 mg) and polyphosphoric acid (1 mL) was heated at 150-160° C. for 24 hours. The mixture was cooled, then diluted with ice water (10 mL) and then treated with ethyl acetate (10 mL). The aqueous layer was basified by addition of solid potassium carbonate. The layers were separated and the aqueous layer was extracted with ethyl acetate (10 mL). The combined organic phases were dried and then evaporated. The residue was subjected to chromatography on silica eluting with a mixture of heptane and ethyl acetate to give 3-(1H-benzoimidazol-2-yl)-1H-indazole (78 mg). LC-MS (METHOD A): RT=1.28 minutes; 235 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (10 mL)
  4. customThe combined organic phases were dried
  5. customevaporated
  6. additionThe residue was subjected to chromatography on silica eluting with a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-649125166cb64f78a405de92765a1540
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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