4-Chloroaniline → (4-Chloro-phenylamino)-phenyl-acetic acid

HRID 1044040

Reaction equation

Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of α-bromophenylacetic acid (1.00 g, 4.65 mmol) in acetonitrile (20 ml), was added 4-chloro-phenylamine (1.18 g, 9.30 mmol), and the mixture was heated under microwave irradiation at 100° C. for 1 hour (UPLC-MS monitoring: complete conversion). The solvent was evaporated, and the residue was positioned between EtOAc and 1N HCl. The organic phase was dried over Na2SO4, filtered and evaporated to dryness to obtain intermediate I11 (0.57 g; 47% yield).

Workup

customThe solvent was evaporated
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
customevaporated to dryness
customto obtain intermediate I11 (0.57 g; 47% yield)

Sources & evidence

ORD record: ord-932593593b624f02a12186934c13286b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563577B2

Linked notes

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