Ethyl chloroformate → HCID 178473418, compound

HRID 1771397Notes

Reaction equation

HRID 1771397 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[OH:13])([O-:3])=[O:2].[C:14](Cl)(=[O:18])[O:15][CH2:16][CH3:17]>N1C=CC=CC=1>[OH:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:9]([C:14]([O:15][CH2:16][CH3:17])=[O:18])[N:8]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 178526496HCID 178526496, compound

Product 1

HCID 178473418HCID 178473418, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-nitro-1H-indazol-3-ol (1.00 g, 5.60 mmol) in pyridine (6.0 mL) was added ethyl carbonochloridate (0.590 μL, 6.14 mmol) and the reaction mixture was heated to 70° C. After 3 hr the reaction mixture was cooled to RT and evaporated in vacuo. The residue was triturated with water (50 mL) to afford ethyl 3-hydroxy-5-nitro-1H-indazole-1-carboxylate as a yellow solid (1.26 g, 85%); Rt 1.70 min (Method 2, acidic); m/z 252 (M+H)+ (ES+).

Workup

  1. temperatureAfter 3 hr the reaction mixture was cooled to RT
  2. customevaporated in vacuo
  3. customThe residue was triturated with water (50 mL)

Sources & evidence

ORD record
ord-96a860fc3c12455ebd5c5fd177fbca61
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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