Sodium Hydroxide → 4-Chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride

HRID 911030Notes

Reaction equation

HRID 911030 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)[CH:15]=1.[OH-].[Na+]>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24826662Ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate

Product 1

HCID 248266634-Chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochlorideYield 184.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the method of Example 31, ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate (0.600 g, 1.54 mmol), ethanol (30 ml), 1M NaOH (10 mL) were combined to give the desired product (0.565 g, 89.4% yield) as a light green solid. 1H NMR (d6-DMSO) δ 8.25 (d, 1H), 7.91 (dd, 1H), 7.83 (d, 1H), 7.81 (d, 1H), 6.66 (dd, 1H), 6.64 (m, 1H), 6.61 (d, 1H), 2.23 (d, 3H).

Sources & evidence

ORD record
ord-323554cbb2614c889133ae92d7b33a15
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…