Lithium Hydroxide → HCID 67253411, compound

HRID 2042107Notes

Reaction equation

HRID 2042107 reaction equation
Cl.[C:2]([C:6]1[N:10]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)[N:9]=[C:8]([C:21]([O:23]CC)=[O:22])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[Li+].[OH-]>C1COCC1>[C:2]([C:6]1[N:10]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)[N:9]=[C:8]([C:21]([OH:23])=[O:22])[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67254744HCID 67254744, compound

Product 1

HCID 67253411HCID 67253411, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 5-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-3-carboxylate hydrochloride (32 g, 0.089 mol) in THF (300 mL) was treated with aqueous LiOH (2 N, 100 mL, 0.20 mmol) and the resultant mixture was heated to 40° C. for 3 hours. The reaction was concentrated under reduced pressure and the remaining aqueous layer was washed with EtOAc. The aqueous phase was acidified to pH 3 and the resultant precipitate was collected by filtration, washed with cold ether and dried in vacuo to provide 5-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-3-carboxylic acid (21 g, 71% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.03 (m, 1H), 8.50 (d, J=8.7 Hz, 1H), 8.20 (d, J=2.4 Hz, 1H), 8.15 (d, J=8.8 Hz, 1H), 7.79 (dd, J=8.7 Hz, 2.4 Hz, 1H), 7.67 (dd, J=8.4, 4.4 Hz, 1H), 6.68 (s, 1H), 1.17 (s, 9H); MS (ESI) m/z: 296.3 (M+H+).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washthe remaining aqueous layer was washed with EtOAc
  3. filtrationthe resultant precipitate was collected by filtration
  4. washwashed with cold ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dfb28bb6ead4490a97b084f70a319ab9
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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