Hydrochloric Acid → Phenyl-o-methylphenylamino-acetic acid hydrochloride

HRID 1044047Notes

Reaction equation

Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.CCN(C(C)C)C(C)C.O.[OH-].[Li+].[ClH:34]>C(#N)C.O1CCOCC1.O>[ClH:34].[C:8]1([CH:2]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:3]([OH:5])=[O:4])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-bromo-2-phenylacetate (0.28 ml, 1.64 mmol), ortho-toluidine (0.26 ml, 2.47 mmol), and DIPEA (0.43 ml, 2.47 mmol) were dissolved in acetonitrile (5 ml) and stirred under microwave irradiation at 100° C. for 1 hours (Conversion complete by UPLC/MS-UV). Lithium hydroxide hydrate (207 mg, 4.94 mmol) and water (3 ml) were added, and the mixture was stirred at room temperature for 16 hours. 4M HCl in dioxane was added until pH was about 1, then the solvents were evaporated, the residue was suspended in water, sonicated, and cooled at 0° C., and the resulting solid was recovered by filtration and dried under vacuum to get intermediate I22 (290 mg, 63% yield).

Workup

stirringthe mixture was stirred at room temperature for 16 hours
customthe solvents were evaporated
customsonicated
temperaturecooled at 0° C.
filtrationthe resulting solid was recovered by filtration
customdried under vacuum
customto get intermediate I22 (290 mg, 63% yield)

Sources & evidence

ORD record: ord-a83dc8177a004444a34cbdb499ebd8f1
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563577B2

Reaction notes

Loading…