Hydrochloric Acid → 4-(2-chloro-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

HRID 1362949Notes

Reaction equation

HRID 1362949 reaction equation
Br[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.[ClH:21]>C1COCC1>[Cl:21][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 313Hydrochloric AcidHCID 58964265N-[4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide

Product 1

HCID 589642634-(2-chloro-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-[4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide (450 mg, 1.33 mmol), concentrated HCl (0.9 mL) in THF (4 mL) was heated with microwave irradiation at 150° C. for 30 minutes. The crude was concentrated in vacuo to give the title compound as a brown oil. Exact mass calculated for C12H14ClN2O 251.1. found 252.0 (MH+). This was used without purification in next step.

Workup

  1. concentrationThe crude was concentrated in vacuo

Sources & evidence

ORD record
ord-9ebbb060caa048e58aa6836a1350c9c4
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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