Sulfuric Acid → 2-Amino-5-[2-(2-methoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl ester

HRID 906583Notes

Reaction equation

HRID 906583 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]([CH2:15][CH2:16][O:17][CH3:18])[N:12]=[CH:13][CH:14]=2)[C:7]([C:19]([F:22])([F:21])[F:20])=[CH:6][C:5]=1[NH:23]C(=O)C.OS(O)(=O)=O>CO>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]([CH2:15][CH2:16][O:17][CH3:18])[N:12]=[CH:13][CH:14]=2)[C:7]([C:19]([F:22])([F:20])[F:21])=[CH:6][C:5]=1[NH2:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 591644302-Acetylamino-5-[2-(2-methoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 591644052-Amino-5-[2-(2-methoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetylamino-5-[2-(2-methoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl ester (352 mg, 0.913 mmol) was treated with MeOH containing 10% of concd H2SO4 (10 mL) and the resultant solution was stirred at 70° C. for 2 h. The solvents were removed in vacuo and the residue was dissolved into water. The pH was adjusted to 10-11 by addition of 2N aq NaOH. The aqueous phase was extracted with AcOEt (2×). The organic phases were combined, dried (Na2SO4) and concentrated in vacuo to afford the title compound (238 mg, 76%). ES-MS: m/z 344.3 [M+H]+, rt 5.52 min.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved into water
  3. additionThe pH was adjusted to 10-11 by addition of 2N aq NaOH
  4. extractionThe aqueous phase was extracted with AcOEt (2×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6725684b71f6491bbd04b542f19d7a29
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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