Sodium Hydroxide → 2-(3-(1H-pyrazol-4-yl)phenyl)acetic acid

HRID 2283494Notes

Reaction equation

HRID 2283494 reaction equation
[OH-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([O:17]CC)=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[N:4]1>O.C1COCC1.CO>[NH:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[N:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86731998ethyl [3-(1H-pyrazol-4-yl)phenyl]acetate

Product 1

HCID 709832172-(3-(1H-pyrazol-4-yl)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

NaOH (57 g, 1.43 mol) was added to a solution of ethyl [3-(1H-pyrazol-4-yl)phenyl]acetate (110 g, 0.478 mol) in H2O/THF/MeOH (250 mL/250 mL/250 mL). The mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo and the pH was adjusted to 3 to 4 via the addition of 3 M HCl, The solid was collected via filtration and dried to afford [3-(1H-pyrazol-4-yl)phenyl]acetic acid. MS ESI calcd. for C11H11N2O2 [M+H]+ 203. found 203. 1H-NMR (500 MHz, DMSO-d6) δ: 7.94 (s, 2H), 7.41-7.24 (m, 2H), 7.13 (t, J=7.6 Hz, 1H), 6.99 (d, J=7.6 Hz, 1H), 3.13 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe pH was adjusted to 3 to 4 via the addition of 3 M HCl
  3. filtrationThe solid was collected via filtration
  4. customdried

Sources & evidence

ORD record
ord-140e13203719459a8ff4069d7b7c3394
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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