Sodium Hydroxide → 4-(2-dimethylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

HRID 919519Notes

Reaction equation

HRID 919519 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][C:7]=1[C:16]1[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=1.[OH-].[Na+]>C(O)C.O>[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[C:16]1[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69494878N-[4-(2-dimethylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide

Product 1

HCID 231395324-(2-dimethylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamineYield 87.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Compound N-[4-(2-dimethylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide (0.50 g, 1.7 mmol) was dissolved in ethanol (25 mL), sodium hydroxide (1.5 g, pallets) in 8 mL of water was added and reaction mixture stirred at 80° C. overnight then concentrated. Water and brine were added then extracted with EtOAc four times. Organic layers were combined, dried over anhydrous Na2SO4 then solvent removed under reduced pressure to afford 4-(2-dimethylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine as a light brown oil in 87.5% yield. LCMS m/z (%)=261 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ: 9.82 (s, 1H), 9.71 (bs, 1H), 7.48-7.45 (m, 3H), 6.93 (d, J=8.74 Hz, 1H), 6.23 (s, 1H), 3.7 (s, 3H), 2.0 (s, 3H).

Workup

  1. customreaction mixture
  2. concentrationthen concentrated
  3. additionWater and brine were added
  4. extractionthen extracted with EtOAc four times
  5. dry with materialdried over anhydrous Na2SO4
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-0114af5510814d03b5043bc886fc1ef3
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

Loading…