3-hydroxy-N-methylbenzamide → Methyl 5-chloro-2-({3-[(methylamino)carbonyl]phenoxy}methyl)benzoate

Reaction equation

BrC[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[OH:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([NH:21][CH3:22])=[O:20]>>[Cl:14][C:11]1[CH:12]=[CH:13][C:4]([CH2:3][O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:18]([C:19]([NH:21][CH3:22])=[O:20])[CH:17]=2)=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

Reactant 2

HCID 3537103-hydroxy-N-methylbenzamide

HCID 68983888Methyl 2-(bromoethyl)-5-chlorobenzoate

Product 1

HCID 68862436Methyl 5-chloro-2-({3-[(methylamino)carbonyl]phenoxy}methyl)benzoate

Procedure

The title compound was prepared according to the procedure described in step 1 of Example 1 from methyl 2-(bromoethyl)-5-chlorobenzoate and 3-hydroxy-N-methylbenzamide (WO 2003018566):

Sources & evidence

ORD record: ord-ea53f5c3df3e45adbd4e80f1a906863f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084476B2

Reaction notes

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