2-Chlorobenzoic Acid → HCID 9951634, compound

HRID 488488Notes

Reaction equation

HRID 488488 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu].[Cu]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23]([OH:25])=[O:24])=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 142560244-(3,4-Dimethoxyphenethyl)aniline

Product 1

HCID 9951634HCID 9951634, compoundYield 33.3%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 4-[2-(3,4-dimethoxy-phenyl)-ethyl]phenylamine (9.25 g, 0.036 mol), 2-chlorobenzoic acid (5.2 g, 0.036 mol), anhydrous potassium carbonate (15.0 g, 0.11 mol), copper powder (0.45 g, 0.007 mol), and a catalytic amount of copper(I) chloride in dry DMF (75 mL) using the procedure described in Example 1, Step C, Method B. After crystallization with MeOH/H2O, 4.5 g (0.012 mol, 33%) of the desired product was obtained mp: 137-139° C.

Workup

  1. customAfter crystallization with MeOH/H2O

Sources & evidence

ORD record
ord-8105db5d3d104816b1b8f2a17ef8bc5b
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

Loading…