Water → N,N-Dimethyl-1H-indazole-3-carboxamide

HRID 2075426Notes

Reaction equation

HRID 2075426 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.[CH3:13][NH2+:14][CH3:15].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.O>C1COCC1>[CH3:13][N:14]([CH3:15])[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 78250Indazole-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231179241-Hydroxybenzotriazole dimethylammonium salt

Product 1

HCID 20816326N,N-Dimethyl-1H-indazole-3-carboxamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1H-indazole-3-carboxylic acid (45.2 g, 279 mmol) was suspended in THF (500 mL), and to the suspension were added 1-hydroxybenzotriazole dimethylammonium salt (55.7 g, 308 mmol) obtained in a similar manner to the known method [for example, Synthesis, page 285 (1992)] and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (58.9 g, 307 mmol), followed by stirring at room temperature overnight. The reaction mixture was added with water, was extracted with ethyl acetate, and the organic layer was sequentially washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from mixed solvent of acetone/water to obtain N,N-dimethyl-1H-indazole-3-carboxamide (37.7 g, 71%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was sequentially washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized
  6. additionfrom mixed solvent of acetone/water

Sources & evidence

ORD record
ord-6f5e2d1f6bb342a197ed3f32af79ea29
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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