Sulfuric Acid → 4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

HRID 1362972Notes

Reaction equation

HRID 1362972 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[CH:7][C:6]=1[C:15]1[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=1.S(=O)(=O)(O)O>CO>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:15]1[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 58964265N-[4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide

Product 1

HCID 468336804-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamineYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-[4-(2-Bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide (3 g, 8.9 mmole) in methanol (6 mL) was added Sulfuric acid (2.2 mL, 42 mmole, 4.78 eq) at 0° C. while stirring. The reaction mixture was refluxed at 90° C. for 1 hour 20 minutes. Crude was quenched with water, neutralized with saturated sodium hydroxide solution until pH 8, extracted with ethyl acetate, and then concentrated in vacuo to give title compound as a solid (2.6 g, 99%). Exact mass calculated for C12H14BrN3O 295.0. found 296.1 (M+H 79Br, 100), 298.2 (M+H 81Br, 98).

Workup

  1. customCrude was quenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-736b65aa12874cf4927983c7d95e8f88
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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