Water → Methyl 6-chloro-1H-indazole-3-carboxylate

HRID 1827452Notes

Reaction equation

HRID 1827452 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[NH:12]C(=O)C.[N:17](OC(C)(C)C)=O.O>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]2[C:6](=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=2)[NH:12][N:17]=1)=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 23577856HCID 23577856, compound

Product 1

HCID 23577858Methyl 6-chloro-1H-indazole-3-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (2-Acetylamino-4-chloro-phenyl)-acetic acid methyl ester )32.0 g, 133 mmol) in acetic acid (200 mL) stirred at 90 degree Celsius was added tert-butyl nitrite (20.5 mL, 172.3 mmol) over 1 hour. The reaction was poured into water (1.4 L) and the solids were recovered by filtration. The yellow precipitate was dissolved in EtOAc, then washed with saturated NaCl. The organic was dried over MgSO4, filtered, and concentrated to a solid. The solids were triturated with hexanes and filtered to afford the desired material (21.63 g, 77%).

Workup

  1. filtrationthe solids were recovered by filtration
  2. dissolutionThe yellow precipitate was dissolved in EtOAc
  3. washwashed with saturated NaCl
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. customThe solids were triturated with hexanes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b85b7095a4174357b13b9892950cd5a6
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

Loading…