Hydrochloric Acid → HCID 67491632, compound

HRID 537185Notes

Reaction equation

HRID 537185 reaction equation
[CH3:1][NH:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[CH:10]=2)[NH:5][N:4]=1.Cl>O1CCOCC1>[CH3:1][NH:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[NH:5][N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67491401HCID 67491401, compound

Product 1

HCID 67491632HCID 67491632, compoundYield 113.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 3-(methylamino)-1H-indazole-5-carboxylate (60.0 mg, 0.29 mmol) was dissolved in 1,4-dioxane (0.5 mL). 3N Aqueous hydrochloric acid (0.3 mL, 0.9 mmol) was added and the reaction was heated to 100° C. for 11.5 hours. The heat was removed and the reaction was left stirring at room temperature overnight. The reaction was concentrated to give the title compound (63 mg, 95%) as a tan solid. +ESI (M+H) 192.1; 1H NMR (400 MHz, CD3OD, δ): 8.61 (d, J=0.78 Hz, 1H), 8.19 (dd, J=8.80, 1.57 Hz, 1H), 7.38 (d, J=8.80 Hz, 1H), 3.02 (s, 3H).

Workup

  1. customThe heat was removed
  2. waitthe reaction was left
  3. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-0749f02186f44b25bcbf101f7a2e6ab6
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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