4-Chloroaniline → HCID 67094269, compound

HRID 1881152Notes

Reaction equation

HRID 1881152 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14]Br.[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([N:22]2[CH2:14][C:5]3[C:4](=[CH:9][C:8]([O:10][CH3:11])=[C:7]([O:12][CH3:13])[CH:6]=3)[C:3]2=[O:16])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 13837927HCID 13837927, compound

Product 1

HCID 67094269HCID 67094269, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-bromomethyl-4,5-dimethoxy-benzoic acid methyl ester (2.9 g), 4-chloroaniline (1.28 g) and triethylamine (1.4 ml) was refluxed in toluene for six hours. The reaction mixture was stirred in an ice bath, filtered and washed with 1 M hydrochloric acid and water.

Workup

  1. filtrationfiltered
  2. washwashed with 1 M hydrochloric acid and water

Sources & evidence

ORD record
ord-45a12d2fb7b44a2eb5f54fc0d27135e8
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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