O-Phenylenediamine → 1097816-83-5

HRID 2182355Notes

Reaction equation

HRID 2182355 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)+. (b) 3-(5-Methoxy-1H-benzoimidazol-2-yl)-1H-indazole

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-6a225ccafb8d4aaca78107d9fd13bfbc
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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